Paper
NJC
1
N-Benzylquinazolin-2-amine (3al). mp 123–125 1C H NMR 5.1 Hz, 1H, ArH), 7.44 (dt, J = 8.9 Hz and 2.9 Hz, 1H, ArH), 7.27
(500 MHz, CDCl3) d 8.95 (s, 1H, ArH), 7.72–7.66 (m, 2H, ArH), (dd, J = 8.2 Hz and 2.9 Hz, 1H, ArH), 5.26 (br s, 1H, NH), 3.52
7.62 (t, J = 7.0 Hz, 1H, ArH), 7.42 (d, J = 7.4Hz, 2H, ArH), 7.35 (quart, J = 6.6 Hz, 2H, CH2N), 1.65 (quint, J = 7.3 Hz, 2H, CH2),
(t, J = 7.4 Hz, 2H, ArH), 7.30–7.26 (m, 2H, ArH), 5.82 (br s, 1H, 1.46 (sext, J = 7.5 Hz, 2H, CH2), 0.97 (t, J = 7.4 Hz, 3H, CH3); 13
C
NH), 4.79 (d, J = 5.3 Hz, 2H, CH2N); 13C NMR (125 MHz, CDCl3) NMR (125 MHz, CDCl3) d 161.0 (d, JC–F = 4.5 Hz), 159.6, 157.6
d 162.0, 159.6, 152.2, 139.2, 134.2, 128.6, 127.8, 127.5, 127.2, (d, JC–F = 242.7 Hz), 149.3, 127.8 (d, JC–F = 7.8 Hz), 124.0 (d, JC–F
125.6, 122.6, 120.3, 45.6. 25.2 Hz), 119.7 (d, JC–F = 8.2 Hz), 110.5 (d, JC–F = 21.6 Hz), 41.4,
=
N-(4-Methylbenzyl)quinazolin-2-amine (3am). mp 142–143 1C; 31.7, 20.2, 13.8; HRMS-EI (70 eV) m/z calcd for C12H15N3F
1H NMR (500 MHz, CDCl3) d 8.93 (s, 1H, ArH), 7.70–7.65 (m, [M + H]+ 220.1250, found 220.1255.
2H, ArH), 7.61 (d, J = 8.3Hz, 1H, ArH), 7.30 (d, J = 7.7 Hz, 1H,
6-Bromo-N-butylquinazolin-2-amine (3ea). mp 123–124 1C;
ArH), 7.24 (t, J = 7.6 Hz, 2H, ArH), 7.15 (d, J = 7.9 Hz, 2H, ArH), 1H NMR (500 MHz, CDCl3) d 8.87 (s, 1H, ArH), 7.78 (d, J =
5.74 (br s, 1H, NH), 4.73 (d, J = 5.7 Hz, 2H, CH2N), 2.34 (s, 3H, 7.2 Hz, 1H, ArH), 7.70 (dd, J = 9.1 Hz and 2.2 Hz, 1H, ArH), 7.46
CH3); 13C NMR (125 MHz, CDCl3) d 162.1, 159.4, 152.1, 136.8, (d, J = 9.0 Hz, 1H, ArH), 5.32 (brs, 1H, NH), 3.52 (quart, J = 6.6
136.0, 134.2, 129.2, 127.8, 127.5, 125.6, 122.6, 120.3, 45.7, 21.3; Hz,2H, CH2N), 1.67 (quint, J = 8.1 Hz, 2H, CH2), 1.45 (sext, J =
HRMS-EI (70 eV) m/z calcd for C16H16N3 [M + H]+ 250.1344, 7.4 Hz, 2H, CH2), 0.97 (t, J = 7.2 Hz, 3H, CH3); 13C NMR
found 250.1349.
(125 MHz, CDCl3) d 160.9, 159.8, 151.2, 137.3, 129.5, 127.5,
N-(4-(Trifluoromethyl)benzyl)quinazolin-2-amine (3an). mp 121.1, 114.9, 41.6, 31.8, 20.3, 13.9; HRMS-EI (70 eV) m/z calcd
152–153 1C; 1H NMR (500 MHz, CDCl3) d 8.96 (s, 1H, ArH), for C12H15N3Br [M + H]+ 280.0449, found 280.0454.
7.71–7.67 (m, 2H, ArH), 7.60–7.58 (m, 3H, ArH), 7.52 (d, J =
N-Butyl-4-phenylquinazolin-2-amine (3fa). mp 72–74 1C;
8.1 Hz, 2H, ArH), 7.26 (t, J = 7.5 Hz, 1H, ArH), 5.82 (br s, 1H, 1H NMR (500 MHz, CDCl3) d 7.78 (d, J = 8.6 Hz, 1H, ArH),
NH), 4.85 (d, J = 6.3 Hz, 1H, CH2N); 13C NMR (125 MHz, CDCl3) 7.70–7.63 (m, 4H, ArH), 7.56–7.52 (m, 3H, ArH), 7.16–7.13 (m,
d 162.1, 159.4, 152.0, 143.6, 134.3, 129.5 (quart, JC–F = 29.2 Hz), 1H, ArH), 5.29 (br s, 1H, NH), 3.57 (quart, 2H, J = 6.6 Hz, CH2N),
127.8, 127.5, 125.7, 125.5, 124.2 (quart, JC–F = 270.8 Hz), 122.9, 1.67 (quint, J = 7.2 Hz, 2H, CH2),1.47 (sext, J = 7.5Hz, 2H, CH2),
120.5, 45,1; HRMS-EI (70 eV) m/z calcd for C16H13N3F3 [M + H]+ 0.98 (t, J = 7.4 Hz, 3H, CH3); 13C NMR (125 MHz, CDCl3) d 169.9,
304.1062 found 304.1072.
159.1, 153.4, 137.5, 133.6, 129.6, 129.4, 128.4, 127.4, 126.1,
N-(Thiophen-2-ylmethyl)quinazolin-2-amine
(3ao).
mp 122.1, 118.4, 41.3, 31.8, 20.1, 13.9; HRMS-EI (70 eV) m/z calcd
136–138 1C; 1H NMR (500 MHz, CDCl3) d 8.94 (s, 1H, ArH), for C18H20N3 [M + H]+ 278.1657, found 278.1661.
7.71–7.63 (m, 3H, ArH), 7.26 (t, J = 7.6 Hz, 1H, ArH), 7.20 (d, J =
N-Butylpyrimidin-2-amine (3ga) (ref. 15). Oil, 1H NMR
5.0 Hz, 1H, ArH), 7.07 (d, J = 2.9 Hz, 1H, ArH), 6.96 (t, J = 4.3 Hz, (500 MHz, CDCl3) d 8.26 (d, J = 4.5 Hz, 2H, CH, ArH), 6.48 (t,
1H, ArH), 5.79 (br s, 1H, NH), 4.94 (d, J = 6.0 Hz, 2H, CH2N); J = 4.8 Hz, 1H, ArH), 5.62 (br s, 1H, NH), 3.40 (quart, J = 6.6 Hz,
13C NMR (125 MHz, CDCl3) d 162.0, 159.1, 152.0, 142.1, 134.2, 2H, CH2N), 1.60 (quint, J = 7.4 Hz, 2H, CH2), 1.42 (sext, J =
127.6, 126.7, 125.7, 125.6, 124.9, 122.8, 120.4, 40.6; HRMS-EI 7.5 Hz, 2H, CH2), 0.94 (t, J = 7.4 Hz, 3H, CH3); 13C NMR
(70 eV) m/z calcd for C13H12N3S [M + H]+ 242.0752 found (125 MHz, CDCl3) d 162.5, 158.0, 110.2, 41.1, 31.6, 20.1, 13.7.
242.0753.
N-Butyl-5-phenylpyrimidin-2-amine (3ha). mp 88–90 1C;
N-Butyl-6-methoxyquinazolin-2-amine (3ba). mp 86–87 1C; 1H NMR (500 MHz, CDCl3) d 8.52 (s, 2H, ArH), 7.47 (d, J =
1H NMR (500 MHz, CDCl3) d 8.88 (s, 1H, ArH), 7.53 (d, J = 7.3 Hz, 2H, ArH), 7.44 (t, J = 7.6 Hz, 2H, ArH), 7.34 (t, J = 7.2 Hz,
9.1 Hz, 1H, ArH),7.35 (dd, J = 9.3 Hz and 2.7 Hz, 1H, ArH), 6.96 1H, ArH), 5.25 (br s, 1H, NH), 3.46 (quart, J = 6.6 Hz, 2H, CH2N),
(d, J = 2.6 Hz, 1H, ArH), 5.11 (br s, 1H, NH), 3.86 (s, 3H, OCH3), 1.63 (quint, J = 7.4 Hz, 2H, CH2), 1.45 (sext, J = 7.5 Hz, 2H, CH2),
3.52 (quart, J = 6.6 Hz, 2H, CH2N), 1.65 (quint, J = 7.3 Hz, 2H, 0.97 (t, J = 7.4 Hz, 3H, CH3); 13C NMR (125 MHz, CDCl3) d 161.9,
CH2), 1.46 (sext, J = 7.4Hz, 2H, CH2), 0.97 (t, J = 7.3 Hz, 3H, 156.3, 135.7, 129.1, 127.2, 125.8, 123.6, 41.4, 31.9, 20.2, 13.7;
CH3); 13C NMR (125 MHz, CDCl3) d 160.3, 159.1, 154.8, 148.2, HRMS-EI (70 eV) m/z calcd for C14H18N3 [M + H]+ 228.1501,
127.1, 126.5, 120.2, 105.1, 55.5, 41.4, 31.8, 20.2, 13.8; HRMS-EI found 228.1502.
(70 eV) m/z calcd for C13H18N3O [M + H]+ 230.1657, found
230.1654.
N-Butyl-5-phenoxypyrimidin-2-amine (3ia). mp 43–44 1C;
1H NMR (500 MHz, CDCl3) d 8.14 (s, 2H, ArH), 7.31 (t, J =
N-Butyl-6-(trifluoromethyl)quinazolin-2-amine (3ca). mp 7.5 Hz, 2H, ArH), 7.06 (t, J = 7.2 Hz, 1H, ArH), 6.93 (d, J = 7.6 Hz,
104–106 1C; 1H NMR (500 MHz, CDCl3) d 9.00 (s, 1H, ArH), 2H, ArH), 5.12 (br s, 1H, NH), 3.40 (quart, J = 6.7 Hz, 2H, CH2N),
7.93 (s, 1H, ArH), 7.81 (dd, J = 8.8 Hz and 1.9 Hz, 1H, ArH), 7.65 1.61 (quint, J = 7.4 Hz, 2H, CH2), 1.43 (sext, J = 7.4 Hz, 2H, CH2),
(s, 1H, ArH), 5.49 (br s, 1H, NH), 3.56 (quart, J = 6.6 Hz, 2H, 0.96 (t, J = 7.4 Hz, 3H, CH3); 13C NMR (125 MHz, CDCl3) d 159.7,
CH2N), 1.67 (quint, J = 7.4 Hz, 2H, CH2), 1.46 (sext, J = 7.4 Hz, 158.5, 151.0, 142.6, 130.0, 122.9, 116.5,41.6, 31.7, 20.2, 13.7;
2H, CH2), 0.98 (t, J = 7.4 Hz, 3H, CH3); 13C NMR (125 MHz, HRMS-EI (70 eV) m/z calcd for C14H18N3O [M + H]+ 244.1450,
CDCl3) d 162.5, 160.6, 153.8, 129.7, 126.6, 125.5, 124.1 (quart, found 244.1452.
JC–F = 33.3 Hz), 124.1 (quart, JC–F = 270.8Hz), 118.8, 41.3, 31.5,
N-Butyl-4,6-diphenylpyrimidin-2-amine (3ja) (ref. 16). mp
20.1, 13.8; HRMS-EI (70 eV) m/z calcd for C13H15N3F3 [M + H]+ 75–76 1C (lit.16 mp 65–66 1C); 1H NMR (500 MHz, CDCl3) d
270.1218, found 270.1219.
8.09–8.08 (m, 4H, ArH), 7.51–7.47(m, 6H, ArH), 7.39 (s, 1H, ArH),
N-Butyl-6-fluoroquinazolin-2-amine (3da). mp 83–84 1C; 1H NMR 5.25 (t, J = 5.4 Hz, 1H, NH), 3.60 (quart, J = 6.6 Hz, 2H, CH2N),
(500 MHz, CDCl3) d 8.91 (s, 1H, ArH), 7.59 (dd, J = 9.2 Hz and 1.68 (quint, J = 7.3 Hz, 2H, CH2), 1.48 (sext, J = 7.4 Hz, 2H, CH2),
c
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2013
New J. Chem., 2013, 37, 624--631 629