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3.3.6. 3,6-Diphenyl-5-(4-fluorobenzylamino)-2-thioxo-2,3-
dihydrothiazolo[4,5-d] pyrimidin-7(6H)-one (5f)
3.3.11. 6-(4-Fluorophenyl)-5-(2-methylbenzylamino)-3-
phenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-
7(6H)-one (5k)
Yellow crystal, yield 77.2%, mp 255.3–256.8 8C; IR (KBr):
y 3376, 2956, 1673, 1542 cmÀ1; 1H NMR (400 MHz, CDCl3):
d 1.99 (s, 3H, CH3), 4.20 (d, 2H, J = 5.6 Hz, CH2), 4.69 (s, 1H,
NH), 6.70–7.59 (m, 13H, Ph-H); Elemental Anal. Calcd. for
C25H19FN4OS2: C, 63.27; H, 4.04; N, 11.81; S, 13.51. Found:
C, 63.58; H, 4.09; N, 11.56; S, 13.59.
Yellow crystal, yield 78.3%, mp 260.4–261.2 8C; IR (KBr) y
3399, 2954, 1676, 1546 cmÀ1; 1H NMR (400 MHz, CDCl3): d
4.11 (d, 2H, J = 6.0 Hz, CH2), 4.89 (s, 1H, NH), 6.75–7.64 (m,
14H, Ph-H); EI-MS (70 eV, m/z): 460 (M+, 38), 351 (12), 185
(25), 109 (100), 103 (24), 91 (21), 77 (50); Elemental Anal.
Calcd. for C24H17FN4OS2: C, 62.59; H, 3.72; N, 12.17; S,
13.92. Found: C, 62.26; H, 3.54; N, 12.29; S, 14.21.
3.3.7. 6-(4-Fluorophenyl)-5-(n-propylamino)-3-phenyl-2-
thioxo-2,3-dihydrothiazolo [4,5-d]pyrimidin-7(6H)-one
(5g)
3.3.12. 6-(4-Fluorophenyl)-5-(3-methylbenzylamino)-3-
phenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-
7(6H)-one (5l)
Yellow crystal, yield 82.4%, mp 231.1–232.7 8C; IR (KBr):
Yellow crystal, yield 73.8%, mp 261.2–263.1 8C; IR (KBr):
y 3366, 2933, 1675, 1543 cmÀ1; 1H NMR (400 MHz, CDCl3):
d 2.27 (s, 3H, CH3), 4.16 (d, 2H, J = 6.0 Hz, CH2), 4.79 (s, 1H,
NH), 6.65–7.60 (m, 13H, Ph-H); EI-MS (70 eV, m/z): 474 (M+,
94), 367 (15), 199 (56), 136 (20), 105 (100), 95 (17), 77 (75);
Elemental Anal. Calcd. for C25H19FN4OS2: C, 63.27; H, 4.04;
N, 11.81; S, 13.51. Found: C, 63.54; H, 3.79; N, 11.49; S,
13.67.
1
y 3336, 2955, 1682, 1597, 1551 cmÀ1; H NMR (400 MHz,
CDCl3): d 0.68 (t, 3H, J = 7.2 Hz, CH3), 1.34 (q, 2H,
J = 7.2 Hz, CH2), 3.01 (q, 2H, J = 6.8 Hz, NHCH2), 4.37 (s,
1H, NH), 7.28–7.58 (m, 9H, Ph-H); EI-MS (70 eV, m/z): 412
(M+, 100), 369 (96), 275 (11), 136 (71), 95 (46), 77 (64);
Elemental Anal. Calcd. for C20H17FN4OS2: C, 58.23; H, 4.15;
N, 13.58; S, 15.55. Found: C, 58.59; H, 4.26; N, 13.47; S, 15.48.
3.3.8. 6-(4-Fluorophenyl)-5-(n-butylamino)-3-phenyl-2-
thioxo-2,3-dihydrothiazolo[4,5-d] pyrimidin-7(6H)-one
(5h)
3.3.13. 6-(4-Fluorophenyl)-5-(4-methylbenzylamino)-3-
phenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-
7(6H)-one (5m)
Yellow crystal, yield 78.6%, mp 250.6–252.1 8C; IR (KBr):
y 3347, 2951, 1682, 1552 cmÀ1; 1H NMR (400 MHz, CDCl3):
d 0.74 (t, 3H, J = 7.2 Hz, CH3), 1.02–1.17 (m, 2H, CH2), 1.26–
1.34 (m, 2H, CH2), 3.04 (q, 2H, J = 6.8 Hz, NHCH2), 4.37 (s,
1H, NH), 7.27–7.58 (m, 9H, Ph-H); EI-MS (70 eV, m/z): 426
(M+, 100), 369 (92), 275 (9), 136 (67), 109 (43), 95 (42), 77
(59); Elemental Anal. Calcd. for C21H19FN4OS2: C, 59.13; H,
4.49; N, 13.14; S, 15.04. Found: C, 59.58; H, 4.76; N, 13.26; S,
14.94.
Yellow crystal, yield 76.5%, mp 255.7–257.1 8C; IR (KBr):
y 335, 2940, 1680, 1546 cmÀ1; 1H NMR (400 MHz, CDCl3): d
2.30 (s, 3H, CH3), 4.13 (d, 2H, J = 5.6 Hz, CH2), 4.80 (s, 1H,
NH), 6.74–7.62 (m, 13H, Ph-H); EI-MS (70 eV, m/z): 474 (M+,
100), 369 (35), 199 (60), 136 (27), 109 (20), 95 (21), 77 (60);
Elemental Anal. Calcd. for C25H19FN4OS2: C, 63.27; H, 4.04;
N, 11.81; S, 13.51. Found: C, 63.55; H, 4.37; N, 11.94; S,
13.45.
3.3.14. 6-(4-Fluorophenyl)-5-(4-methoxybenzylamino)-3-
phenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-
7(6H)-one (5n)
Yellow crystal, yield 69.8%, mp 230.7–231.6 8C; IR (KBr):
y 3316, 2939, 1678, 1545 cmÀ1; 1H NMR (400 MHz, CDCl3):
d 3.77 (s, 3H, CH3), 4.11 (d, 2H, J = 6.0 Hz, CH2), 4.78 (s, 1H,
NH), 6.70–7.63 (m, 13H, Ph-H); EI-MS (70 eV, m/z): 490 (M+,
100), 121 (50), 77 (8); Elemental Anal. Calcd. for
C25H19FN4O2S2: C, 61.21; H, 3.90; N, 11.42; S, 13.07. Found:
C, 61.43; H, 4.16; N, 11.20; S, 13.21.
3.3.9. 6-(4-Fluorophenyl)-5-(iso-butylamino)-3-phenyl-2-
thioxo-2,3-dihydrothiazolo [4,5-d]pyrimidin-7(6H)-one (5i)
Yellow crystal, yield 71.6%, mp 256.2–257.4 8C; IR (KBr):
1
y 3339, 2959, 1678, 1576, 1547 cmÀ1; H NMR (400 MHz,
CDCl3): d 0.67 (d, 6H, J = 6.8 Hz, 2CH3), 1.63–1.66 (m, 1H,
CH), 2.87 (t, 2H, J = 6.4 Hz, CH2), 4.42 (s, 1H, NH), 7.27–7.58
(m, 9H, Ph-H); EI-MS (70 eV, m/z): 426 (M+, 75), 369 (100),
275 (4), 136 (29), 109 (15), 95 (21), 77 (26); Elemental Anal.
Calcd. for C21H19FN4OS2: C, 59.13; H, 4.49; N, 13.14; S,
15.04. Found: C, 59.13; H, 4.49; N, 13.14; S, 15.04.
3.3.15. 5-(4-Chlorobenzylamino)-6-(4-fluorophenyl)-3-
phenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]pyrimidin-
7(6H)-one (5o)
3.3.10. 6-(4-Fluorophenyl)- 3-phenyl-5-(tert-butylamino)-
2-thioxo-2,3-dihydrothiazolo [4,5-d]pyrimidin-7(6H)-one
(5j)
Yellow crystal, yield 87.7%, mp 248.2–249.6 8C; IR
(KBr): y 3295, 2943, 1681, 1543 cmÀ1; 1H NMR (400 MHz,
CDCl3): d 4.12 (d, 2H, J = 6.0 Hz, CH2), 4.88 (s, 1H, NH),
6.73–7.63 (m, 13H, Ph-H); EI-MS (70 eV, m/z): 494 (M+,
18), 219 (40), 191 (11), 136 (27), 109 (10), 77 (15);
Elemental Anal. Calcd. for C24H16ClFN4OS2: C, 58.23; H,
3.26; N, 11.32; S, 12.93. Found: C, 58.27; H, 3.35; N, 11.37;
S, 12.98.
Yellow crystal, yield 69.6%, mp 225.4–227.1 8C; IR (KBr):
1
y 3431, 2969, 1685, 1580, 1548 cmÀ1; H NMR (400 MHz,
CDCl3): d 1.05 (s, 9H, 3CH3), 4.15 (s, 1H, NH), 7.27–7.58 (m,
9H, Ph-H); EI-MS (70 eV, m/z): 426 (M+, 68), 369 (100), 277
(6), 136 (27), 109 (13), 95 (27), 77 (30); Elemental Anal. Calcd.
for C21H19FN4OS2: C, 59.13; H, 4.49; N, 13.14; S, 15.04.
Found: C, 59.59; H, 4.67; N, 13.01; S, 14.68.