396
H.-Q. Wang, M.-W. Ding, Z.-J. Liu, and L.-M. Yang
Vol. 41
1.48 ~ 1.53 (m, 2H, NCH CH Et), 3.35 ~ 3.42 (2H, m, NC H Pr-n,
Anal. Calcd. for C
Found: C, 70.15; H, 5.92; N, 14.26.
H
N OS: C, 70.28; H, 5.90; N, 14.13.
2
2
2
J = 6.6Hz (after the D O exchange) ), 4.32 (t, 1H, J = 5.6Hz, NH),
29 29
5
2
4.47 (s, 2H, SC H Ph), 7.19 ~ 7.59 (m, 13H, P h), 8.16 (d, 2H, J =
2
7.5Hz, P h); IR ( KBr ): ν 3429, 1700, 1595, 1554, 1454, 1385,
3-Benzylthio-6-(2-methylbenzylamino)-1,5-diphenyl-1H- p y r a-
zolo[3,4-d]pyrimidin-4(5H)-one (5h).
-1
1029 cm ; MS (70eV) (relative intensity %): m/z 483 (M+2, 11),
This compound was prepared according to the general proce-
1
dure above to give 5h: H NMR (CDCl , 300 MHz): δ 2.25 (s,
482 (M+1, 35), 481 (M+, 72), 448 (96), 246 (20), 169 (20), 119
(79), 91 (100), 77 (88).
3
3H, PhCH -o), 4.46 (s, 2H, PhCH S), 4.55 (s, 1H, NH), 4.56 (s,
Anal. Calcd: for C
Found: C, 70.02; H, 5.56; N, 14.62.
H N OS: C, 69.83; H, 5.65; N, 14.54.
3
2
2H, CH N), 7.12 ~ 7.58 (m, 17H, Ar), 8.01 (d, 2H, J = 8.4Hz,
28 27 5
2
Ar); IR (KBr): ν 3421, 1709, 1600, 1554, 1386, 1032; MS (70eV)
(relative intensity %): m/z 530 (M+1, 6), 529 (M+, 15), 496 (32),
181 (12), 105 (100), 91 (56), 77 (31).
3-Benzylthio-6-isobutylamino-1,5-diphenyl-1H-pyrazolo[3,4-d]-
pyrimidin-4(5H)-one (5d).
Anal. Calcd. for C
Found: C, 72.71; H, 5.11; N, 13.39.
H N OS: C, 72.56; H, 5.14; N, 13.22.
32 27 5
This compound was prepared according to the general proce-
1
dure above to give 5d: H NMR (CDCl , 300 MHz): δ 0.85 (d,
3
6H, J = 6.6Hz, Me CH), 1.86 ~ 1.93 (m, 1H, Me CHCH N), 3.20
2
(t, 2H, J = 6.2Hz, CHC H N), 4.40 (m, 1H, N H), 4.48 (s, 2H,
2
2
3-Benzylthio-6-(4-methylbenzylamino)-1,5-diphenyl-1H- p y r a-
zolo[3,4-d]pyrimidin-4(5H)-one (5i).
2
PhCH ), 7.19 ~ 7.60 (m,13H, Ph), 8.15 (d, 2H, J = 8.1Hz, Ph);
2
This compound was prepared according to the general proce-
1
dure above to give 5i: H NMR (CDCl , 300 MHz): δ 2.31 (s,
IR (KBr): ν 3441, 1704, 1598, 1548, 1454, 1386, 1034; MS
(70eV) (relative intensity %): m/z 483(M+2,4), 482 (M+1, 12),
481(M+, 34), 448 (88), 246 (12), 169 (12), 119 (51), 91 (100), 77
(62), 57 (22).
3
3H, PhCH -p), 4.46 (s, 2H, PhCH S), 4.52 (d, 2H, J = 4.5Hz,
3
2
CH N), 4.70 (d, 1H, J = 5.1Hz, NH), 7.21 ~ 7.57 (m, 17H, Ar),
2
8.04 (d, 2H, J = 7.5Hz, Ar); IR (KBr): ν 3359, 1686, 1598, 1541,
1361, 1035; MS (70eV) (relative intensity %): m/z 530 (M+1,6),
529 (M+, 14), 496 (31), 181 (20), 105 (100), 91 (59), 77 (33).
Anal. Calcd. for C
H N OS: C, 69.83; H, 5.65; N 14.54.
28 27 5
Found: C, 69.87; H, 5.69; N, 14.66.
6-tert-Butylamino-3-benzylthio-1,5-diphenyl-1H- pyrazolo[3,4-d]-
pyrimidin-4(5H)-one (5 e).
Anal. Calcd. for C
Found: C, 72.47; H, 5.20 ; N, 13.36.
H N OS: C, 72.56; H, 5.14; N, 13.22.
32 27 5
This compound was prepared according to the general proce-
1
dure above to give 5e: H NMR (CDCl , 300 MHz): δ 1.36 (s,
3-Benzylthio-6-(2-fluorobenzylamino)-1,5-diphenyl-1H- p y r a-
zolo[3,4-d]pyrimidin-4(5H)-one (5j).
3
9H, t-Bu), 4.20 (s, 1H, NH), 4.47 (s, 2H, PhCH ), 7.21 ~ 7.56 (m,
2
This compound was prepared according to the general proce-
1
dure above to give 5j: H NMR (CDCl , 300 MHz): δ 4.45 (s,
13H, Ph), 8.09 (d, 2H, J = 7.5Hz, Ph); IR (KBr): ν 3414, 1705,
1598, 1454, 1388, 1034; MS (70eV) (relative intensity %): m/z
483 (M+2, 3), 482 (M+1, 8), 481 (M+, 23), 448 (53), 392 (16),
119 (47), 91 (100), 77 (59).
3
2H, PhCH S), 4.59 (t, 2H, J = 5.4Hz, CH N), 4.84 (t, 1H, J = 5.1
2
2
Hz, NH), 6.99 ~7.60 (m, 17H, Ar), 8.02 (d, 2H, J = 7.5Hz, Ar); IR
(KBr): ν 3364, 1694, 1590, 1360, 1032; MS (70eV) (relative
intensity %): m/z 535 (M+2, 3), 534 (M+1, 8), 533 (M+, 24), 500
(53), 392 (16), 109 (64), 91 (100), 77 (19).
Anal. Calcd. for C
Found: C, 69.82; H, 5.76; N, 14.70.
H N OS: C, 69.83; H, 5.65; N, 14.54.
28 27 5
Anal. Calcd. for C
H FN OS: C, 69.77; H, 4.53; N, 13.12.
3-Benzylthio-6-diethylamino-1,5-diphenyl-1H-pyrazolo[3, 4-d]-
pyrimidin-4(5H)-one (5f).
31 24 5
Found: C, 69.65; H, 4.60; N, 13.25.
3-Benzylthio-6-(4-fluorobenzylamino)-1,5-diphenyl-1H- p y r a-
zolo[3,4-d]pyrimidin-4(5H)-one (5k).
This compound was prepared according to the general pro-
1
cedure above to give 5 f: H NMR (CDCl , 300 MHz): δ 0.87
3
(t, 6H, J = 6.9Hz, CH CH ), 3.15 (q, 4H, J = 6.9Hz, CH CH ),
2
4.46 (s, 2H, PhC H ), 7.18 ~ 7.47 (m,13H, P h), 8.13 (d, 2H, J =
3
2
3
This compound was prepared according to the general proce-
1
dure above to give 5k: H NMR (CDCl , 300 Hz): δ 4.51 (s, 2H,
2
3
PhCH S), 5.37 (s, 2H, CH N), 6.49 (s, 1H, NH), 6.94 ~7.49 (m,
7.8Hz, Ph); IR (KBr): ν 1699, 1601, 1555, 1454, 1392, 1033;
MS (70eV) (relative intensity %): m/z 483 (M+2, 5), 482
(M+1, 17), 481 (M+, 49), 448 (90), 345 (10), 119 (37), 91
(100), 77 (66).
2
2
17H, A r) , 8.03 (d, 2H, J=8.1Hz, Ar); IR(KBr): ν 3303, 1675,
1594, 1555, 1386; MS (70eV) (relative intensity %): m/z 535
(M+2, 3), 534 (M+1, 9), 533 (M+, 26), 500 (54), 109 (66), 91
(100), 77 (20).
Anal. Calcd. for C
Found: C, 69.86; H, 5.71; N, 14.60.
H N OS: C, 69.83; H, 5.65; N, 15.54.
28 27 5
Anal. Calcd. for C
H FN OS: C, 69.77; H, 4.53; N 13.12.
31 24 5
Found: C, 69.86; H, 4.49; N, 13.22.
3-Benzylthio-6-pentylamino-1,5-diphenyl-1H-pyrazolo[3, 4-d]-
pyrimidin-4(5H)-one (5g).
3-Benzylthio-6-(2-chlorobenzylamino)-1,5-diphenyl-1H- p y r a-
zolo[3,4-d]pyrimidin-4(5H)-one (5l).
This compound was prepared according to the general pro-
1
cedure above to give 5g: H NMR (CDCl , 300 MHz): δ 0.87
This compound was prepared according to the general proce-
1
dure above to give 5l: H NMR (CDCl , 300 MHz): δ 4.45 (s,
3
(t, 3H, J = 6.9Hz, N(CH ) C H ), 1.22 ~ 1.31 (m, 4H,
2 4
NCH CH CH CH CH ), 1.52 ~ 1.54 (m, 2H, NCH CH CH ),
3
3
2H, PhCH S), 4.60 (t, 2H, J = 5.7Hz, CH N), 4.99 (t, 1H, J =
2
2
2
2
3
2
2
2
3.34 ~ 3.40 (m, 2H, NC H CH ), 4.33 (s, 1H, NH ), 4.47 (s,
2
2
5.4Hz, NH), 7.13 ~ 7.60 (m, 17H, Ar), 8.01 (d, 2H, J = 7.8Hz,
Ar); IR (KBr): ν 3356, 1695, 1598, 1538, 1358, 1023; MS (70eV)
(relative intensity %): m/z 551 (M+1, 13), 549 (M+, 31), 516
(67), 127 (32), 125 (100), 91 (97), 77 (42).
2
2H, PhC H ), 7.17 ~ 7.58 (m, 13H, P h), 8.16 (d, 2H, J = 8.1Hz,
2
2
Ph); IR (KBr): ν 3430, 1702, 1595, 1565, 1497, 1385, 1035;
MS (70eV) (relative intensity %): m/z 497 (M+2, 7), 496 (
M+1, 21), 495 (M+, 54), 463 (45), 462 (87), 119 (54), 91
(100), 77 (64).
Anal. Calcd. for C
H ClN OS: C, 67.69; H, 4.40; N, 12.73.
31 24 5
Found: C, 67.48; H, 4.42; N, 12.91.