Notes
J . Org. Chem., Vol. 65, No. 12, 2000 3867
NMR: δ ) 9.17 (s, 1H, NH), 7.68 (s, 1H, NH), 7.15 (d, ÅJ ) 8.6
Hz, 2H; arom CH), 6.88 (d, J ) 8.5 Hz, 2H; arom CH), 5.09 (s,
1H, CH), 3.98 (q, J ) 7.0 Hz, 2H, OCH2), 3.71 (s, 3H, OCH3),
2.24 (s, 3H, CH3), 1.10 (t, J ) 7.0 Hz, 3H, CH3); IR (KBr): 3241,
1700, 1637 cm-1. Anal. Calcd for C15H18N2O4: C, 62.07; H, 6.20;
N, 9.66. Found: C, 61.65; H, 6.21; N 9.58.
1.38-1.15 (m, 9H, (CH2)3CH3), 0.85 (t, J ) 6.3 Hz, 3H, CH3);
13C NMR: δ ) 165.4, 152.7, 148.2, 99.4, 59.7, 59.0, 49.90, 36.4,
25.9, 21.9, 20.7, 17.6, 14.2, 14.0; IR (KBr): 3248, 1722, 1647
cm-1; MS (70 eV, EI): m/z (%): 241 (M + 1, 12), 183 (100). Anal.
Calcd for C11H20N2O3: C, 59.96; H, 8.39; N, 11.66. Found: C,
58.58; H, 8.13; N 11.57.
5-(Eth oxyca r bon yl)-6-m eth yl-4-(4-n itr op h en yl)-3,4-d ih y-
d r op yr im id in -2(1H)-on e (7c): mp 207-210 °C; 1H NMR: δ
) 9.37 (s, 1H, NH), 8.23 (d, J ) 8.76 Hz, 2H, arom CH), 7.91 (s,
1H, NH), 7.52 (d, J ) 8.69 Hz, 2H, arom CH), 5.28 (d, J ) 3.2
Hz, 1H, CH), 3.99 (q, J ) 7.1 HZ, 2H, OCH2), 2.27 (s, 3H, CH3),
1.10 (t, J ) 7.1 Hz, 3H, CH3); IR (KBr): 3235, 2981, 1724,1702,
1645, 1594 cm-1. Anal. Calcd for C14H15N3O5: C, 55.08; H, 4.92;
N, 13.77. Found: C, 54.80; H, 4.95; N, 13.77.
5-(E t h oxyca r b on yl)-4-isop r op yl-6-m et h yl-3,4-d ih yd r o-
p yr im id in -2(1H)-on e (7k ): mp 194-195 °C; 1H NMR: δ ) 8.86
(s, 1H, NH), 7.26 (s, 1H, NH), 4.04 (m, 2H, OCH2), 3.96 (t, J )
3.6 Hz, 1H, CH), 2.18 (s, 3H, CH3), 1.68 (m, 1H, CH), 1.19 (t, J
) 7.1 Hz, 3H, CH3), 0.82 (d, J ) 6.9 Hz, 3H, CH3), 0.74 (d, J )
6.8 Hz, 3H, CH3); 13C NMR: δ ) 165.8, 153.2, 148.4, 98.2, 59.1,
55.5, 34.6, 18.5, 17.7, 16.0, 14.2; IR (KBr): 3234, 3106, 1692,
1645 cm-1; MS (70 eV, EI): m/z (%): 227 (M + 1, 54), 183 (100).
Anal. Calcd for C11H18N2O3: C, 58.39; H, 8.02; N, 12.38. Found:
C, 58.40; H, 8.01; N, 12.44.
5-Aceto-6-m eth yl-4-p h en yl-3,4-d ih yd r op yr im id in -2(1H)-
on e (7l): mp 233-236 °C; 1H NMR: δ ) 9.16 (s, 1H, NH), 7.78
(s, 1H, NH), 7.22-7.36 (m,5H, arom CH), 5.25 (d, J ) 2.4 Hz,
1H, CH), 2.24 (s, 3H, CH3CO), 2.07 (s, 3H, CH3); 13C NMR: δ )
194.4, 158.5, 152.1, 147.8, 136.9, 127.7, 113.9, 109.6, 55.1, 53.3,
30.18, 18.8; IR (KBr): 3257 1699, 1673 cm-1; MS (70 eV, EI):
m/z (%): 230 (M, 57), 229 (M - 1, 100); HRMS for C13H14N2O2:
230.1102; found 230.1055.
5-Aceto-6-m eth yl-4-(4-m eth oxyp h en yl)-3,4-d ih yd r op yr i-
m id in -2(1H)-on e (7m ): mp 168-130 °C; 1H NMR: δ ) 9.16 (s,
1H, NH), 7.78 (s, 1H, NH), 7.16 (d, J ) 8.7 HZ, 2H, arom CH),
6.88 (d, J ) 8.7 Hz, 2H, arom CH), 5.20 (d, J ) 3.0 Hz, 1H, CH),
3.72 (s, 3H, CH3CO), 2.28 (s, 3H, CH3), 2.07 (s, 3H, OCH3); 13C
NMR: δ ) 194.4, 158.5, 152.1, 147.8, 136.4, 127.7, 113.9, 109.6,
55.1, 53.3, 30.2, 18.8; IR (KBr): 3242, 1714, 1624,cm-1; MS (70
eV, EI): m/z (%): 260 (M, 44), 259 (M - 1, 100); HRMS for
C14H16N2O3: 260.1133; found 260.1160
5-Acetyl-6-m eth yl-4-(4-n itr op h en yl)-3,4-d ih yd r op yr im i-
d in -2(1H)-on e (7n ): mp 230 (dec); 1H NMR: δ ) 9.40 (s, 1H,
NH), 8.21 (d, J ) 8.4 Hz, 2H, arom,CH), 7.93 (s, 1H, NH), 7.51
(d, J ) 8.7 Hz, 2H, arom CH), 5.39 (s, 1H, CH), 2.32 (s, 3H,
CH3CO), 2.19 (s, 3H, CH3); 13C NMR: δ ) 194.0, 152.0, 151.6,
149.1, 146.7, 127.7, 123.8, 109.5, 53.1, 30.7, 19.1; IR (KBr): 3241,
1699, 1627 cm-1; MS (70 eV, EI): m/z (%): 275 (M, 29), 274 (M
- 1, 43), 153 (100); HRMS for C13H13N3O: 275.0937; found
275.0906.
5-Ben zoyl-4-p h en yl-h exa h yd r op yr im id in e (6o): mp 198-
200 °C; 1H NMR: δ ) 7.67 (m, 2H, NH), 7.51-7.10 (m, 10H,
arom CH), 4.98 (d, J ) 11.1 Hz, 1H, CH), 4.39 (d, J ) 11.1 Hz,
1H, CH); 13C NMR: δ ) 195.8, 154.0, 138.4, 137.3, 133.4, 128.6,
128.4, 128.3, 127.8, 81.7, 54.7, 48.1; IR (KBr): 3220, 1718, 1684
cm-1; MS (70 eV, EI): m/z (%): 365 (M+1, 1), 241 (100), 207
(25). Anal. Calcd for C18H13N2O3F3: C, 59.34; H, 4.15; N, 7.96.
Found: C, 59.32; H, 4.15; N, 7.64.
5-Ben zoyl-4-p h en yl-6-tr iflu or om eth yl-3,4-d ih yd r op yr i-
m id in -2(1H)-on e (7o): mp 160-162 °C; 1H NMR: δ ) 9.86 (s,
1H, NH), 7.93 (s, 1H, NH), 7.66 (m, 3H, arom, CH), 7.48 (m,
2H, arom, CH), 7.25 (m, 5H, arom, CH), 5.22 (s, 1H, CH); 13C
NMR: δ ) 192.4, 151.9, 141.1, 135.9, 134.1, 128.9, 128.8, 128.3
126.6, 114.6,57.1; IR (KBr): 3246, 1705, 1670 cm-1; MS (70 eV,
EI): m/z (%): 345 (M - 1, 4), 346 (M, 14), 77 (100); HRMS for
C18H13N2O2F3: 346.0929; found 346.0922.
4-(4-Ch lor op h en yl)-5-(eth oxyca r bon yl)-6-m eth yl-3,4-d i-
h yd r op yr im id in -2(1H)-on e (7d ): mp 210-212 °C; 1H NMR:
δ ) 9.26 (s, 1H, NH), 7.79 (d, J ) 3.1 Hz, 1H, NH), 7.40 (d, J )
0.5 Hz, 2H arom CH), 7.25 (d, J ) 8.5 Hz, 2H; arom CH), 5.14
(s, 1H, CH), 3.99 (q, J ) 7.0 Hz, 2H, OCH2), 2.25 (s, 3H, CH3),
1.09 (t, J ) 7.0 Hz, 3H, CH3); IR (KBr): 3241, 1700, 1645 cm-1
.
Anal. Calcd for
C14H15N2O3Cl: C, 57.14; H, 5.10; N 9.52.
Found: C, 56.99; H, 5.09; N, 9.60.
4-(4-F lu or op h en yl)-5-(eth oxyca r bon yl)-6-m eth yl-3,4-d i-
h yd r op yr im id in -2(1H)-on e (7e): mp 175-177 °C; 1H NMR:
δ ) 9.25 (s, 1H, NH), 7.77 (s, 1H, NH), 7.21 (m, 4H; arom CH),
5.15 (s, 1H, CH), 3.99 (q, J ) 7.1 Hz, 2H, OCH2), 2.26 (s, 3H,
CH3), 1.09 (t, J ) 7.1 Hz, 3H, CH3); 13C NMR: δ ) 165.3, 162.9,
159.8, 152.0, 148.6, 141.1, 128.3, 115.1, 99.2, 59.3, 53.3, 17.8,
14.1; IR (KBr): 3243, 1698, 1638 cm-1; MS (70 eV, EI): m/z (%):
278 (M, 12), 249 (100). Anal. Calcd for C14H15N2O3F: C, 60.43;
H, 5.40; N, 10.07. Found: C, 60.07; H, 5.50; N, 10.18.
4-(2,4-Dich lor op h en yl)-5-(eth oxyca r bon yl)-6-m eth yl-3,4-
d ih yd r op yr im id in -2(1H)-on e (7f): mp 238-240 °; 1H NMR:
δ ) 9.33 (s, 1H, NH), 7.77 (s, 1H, NH), 7.57 (s, 1H; arom CH),
7.42 (d, J ) 8.4 Hz, 1H, arom CH), 7.32 (d, J ) 8.4 Hz, 1H,
arom CH), 5.60 (s, 1H, CH), 3.90 (q, J ) 7.1 Hz, 2H, OCH2),
2.29 (s, 3H, CH3), 1.00 (t, J ) 7.1 HZ, 3H, CH3); 13C NMR: δ )
165.0, 151.3, 149.7, 141.0, 132.8, 130.4, 128.8, 128.1, 97.6, 59.3,
51.3, 17.8, 14.0; IR (KBr): 3357, 1697, 1635 cm-1; MS (70 eV,
EI): m/z (%): 329 (M, 4), 183 (100). Anal. Calcd for C14H14N2O3-
Cl2: C, 51.08; H, 4.29; N, 8.51. Found: C, 51.14; H, 4.27; N,
8.53.
5-(E t h oxyca r b on yl)-6-m e t h yl-4-(4-(t r iflu or om e t h yl)-
p h en yl)-3,4-d ih yd r op yr im id in -2(1H)-on e (7g): mp 173-175
°C; 1H NMR: δ ) 9.33 (s, 1H, NH), 7.86 (d, J ) 2.9 Hz, 1H,
NH), 7.72 (d, J ) 8.2 Hz, 2H; arom CH), 7.47 (d, J ) 8.2 Hz,
2H; arom CH), 5.25 (d, J ) 2.8 Hz, 1H, CH), 4.00 (q, J ) 7.1 Hz,
2H, OCH2), 2.27 (s, 3H, CH3), 1.12 (t, J ) 7.1 Hz, 3H, CH3); 13
C
NMR: δ ) 165.2, 152.0, 149.3, 149.1, 149.0, 128.3,127.8, 126.9,
126.1, 125.5, 98.6, 59.4, 53.7, 17.8, 14.0; IR (KBr):3237, 1703,
1647 cm-1; MS (70 eV, EI): m/z (%): 328 (M, 12), 183 (100). Anal.
Calcd for C15H15N2O3F3: C, 54.88; H, 4.57; N, 8.54. Found: C,
54.52; H, 4.58; N 8.56.
4-(2-Br om op h en yl)-5-(eth oxyca r bon yl)-6-m eth yl-3,4-d i-
1
h yd r op yr im id in -2(1H)-on e (7h ): mp 206-208 °C; H NMR:
δ ) 9.29 (s, 1H, NH), 7.71 (s, 1H, NH), 7.57 (d, J ) 7.9 Hz, 1H,
arom CH), 7.34 (m, 2H, arom CH), 7.19 (m, 1H, arom CH), 5.61
(d, J ) 2.2 Hz, 1H, CH), 3.89 (q, J ) 7.1 Hz, 2H, OCH2), 2.30 (s,
3H, CH3), 0.99 (t, J ) 7.1 Hz, 3H, CH3); 13C NMR: δ ) 165.0,
151.3, 149.3, 143.4, 132.6, 129.4,128.8 128.4, 122.3, 98.3, 59.1,
54.0, 17.6, and 14.0; IR (KBr): 3344, 1686, 1635 cm-1; MS (70
eV, EI): m/z (%): 339 (M, 21), 42 (100). Anal. Calcd for
C14H15N2O3Br: C, 49.57; H, 4.47; N, 8.26. Found: C, 49.71; H,
4.50; N 8.24.
5-Th ien oyl-4-ph en yl-h exah ydr opyr im idin e (6p): mp 192-
195 °C; 1H NMR: δ ) 7.84 (m, 2H, thiene CH), 7.76 (s, 1H, NH),
7.39 (s, 1H, thiene CH), 7.37 (s, 1H, NH), 7.27 (s, 1H, OH), 7.17-
7.05 (m, 5H, arom, CH), 4.93 (d, J ) 11.2 Hz, 1H, CH), 4.25 (d,
J ) 11.1 Hz, 1H, CH); IR (KBr): 3442, 3202, 1680, 1662 cm-1
;
13C NMR: δ ) 188.3, 153.9, 145.6, 144.9, 138.1, 136.1, 135.4,
133.9, 128.3, 128.1, 127.6, 127.1, 124.6, 121.8, 81.3, 54.4, 49.7.
MS (70 eV, EI): m/z (%): 371 (M - 1, 14), 241 (100); IR (KBr):
3398, 1698, 1683 cm-1. Anal. Calcd for C16H13F3N2O3S: C, 51.89;
H, 3.51; N, 7.56. Found: C, 51.62; H, 3.94; N, 6.88. HRMS for
C16H13F3N2O3S: 370.0659; found 370.0653.
5-(E t h oxyca r b on yl)-6-m et h yl-4-st yr yl-3,4-d ih yd r op yr i-
1
m id in -2(1H)-on e (7i): mp 232-235 °C; H NMR: δ ) 9.13 (s,
1H, NH), 7.53 (d, J ) 1.9 Hz, 1H, NH), 7.21-7.46 (m, 5H, arom
CH), 6.37 (d, J ) 15.9 Hz, 1H, H-CdCH), 6,20 (dd, J ) 15.8,
6.0 Hz, 1H, CHdC-H), 4.74 (d, J ) 5.80 Hz, 1H, CH), 4.09 (m,
2H, OCH2), 2.21 (s, 3H, CH3), 1.20 (t, J ) 7.0 Hz, 3H, CH3); 13
C
NMR: δ ) 165.1, 152.6, 148.5, 136.2, 130.0, 128.6, 128.1, 127.5,
126.2, 97.8, 59.2, 51.8, 17.7, 14.2; IR (KBr): 3241, 1704, 1650
cm-1; MS (70 eV, EI): m/z (%): 286 (M, 17), 259 (100); HRMS
calcd for C16H18N2O3 286.1346; found 286.1317.
4-Bu tyl-5-(eth oxyca r bon yl)-6-m eth yl-3,4-d ih yd r op yr im i-
d in -2(1H)-on e (7j): mp 157-158 °C; 1H NMR: δ ) 8.92 (s, 1H,
NH), 7.31 (s, 1H, NH), 4.05 (m, 2H, OCH2), 2.16 (s, 3H, CH3),
4-P h e n yl-5-t h ie n oyl-6-(t r iflu or om e t h yl)-3,4-d ih yd r o-
p yr im id in -2(1H)-on e (7p ): mp 99-102 °C; 1H NMR: δ ) 9.79
(s, 1H, NH), 8.03 (d, J ) 5.0 Hz, 1H, thiene CH), 7.90 (s, 1H,
NH), 7.52 (d, J ) 3.8 Hz, 1H, thiene CH), 7.34-7.11 (m, 5H,
arom CH), 5.25 (s, 1H, CH); IR (KBr): 3200, 1670 cm-1; MS (70
eV, EI): m/z (%): 353 (M+1, 13), 352 (M, 3), 111 (100); HRMS
for C16H11F3N2O2S: 352.0494; found 352.0456.