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Chapter 4
Synthesis of highly substituted pyrazolopyrimidine
1166, 954, 883, 780, 743, 698 cm -1 ; MS (m/z): 514 (M + ); Anal. Calcd for
C 23 H 26 N 6 O 4 S 2 : C, 53.68; H, 5.09; N, 16.33; Found: C, 53.67; H, 5.04; N, 16.36.
N 3 -cyclohexyl-N 6 -(4-methoxyphenyl)-7-methyl-2,5-bis(methylthio)pyrazolo[1,5-a]
pyrimidine-3,6-dicarboxamide 10g. Creamish solid; mp >320 ° C, R f 0.36 (9:1
Chloroform: Methanol); IR (KBr): 3422, 3127, 3085, 2942, 1628, 1483, 1237, 1158,
883, 780, 743 cm -1 ; MS (m/z): 499 (M + ); Anal. Calcd for C 24 H 29 N 5 O 3 S 2 : C, 57.69; H,
5.85; N, 14.02; Found: C, 57.67; H, 5.84; N, 14.03.
N 3 -cyclohexyl-7-methyl-N 6 -(2,5-dimethylphenyl)-2,5-bis(methylthio)pyrazolo
[1,5-a]pyrimidine-3,6-dicarboxamide 10h. Creamish solid; mp >320 ° C, R f 0.41
(9:1Chloroform: Methanol); IR (KBr): 3430, 3133, 3051, 2922, 1651, 1516, 1483,
1232, 1166, 954, 883, 780, 743, 698 cm -1 ; MS (m/z): 497 (M + ); Anal. Calcd for
C 25 H 31 N 5 O 2 S 2 : C, 60.33; H, 6.28; N, 14.07; Found: C, 60.35; H, 6.25; N, 14.03.
N 3 -cyclohexyl-7-isopropyl-2,5-bis(methylthio)-N 6 -p-tolylpyrazolo[1,5-a]
pyrimidine-3,6-dicarboxamide 10i. White solid; mp >320
° C, R f 0.35
(9:1Chloroform: Methanol); IR (KBr): 3279, 3254, 3016, 2928, 2850, 1730, 1681,
1566, 1313, 1246, 835, 810, 748, 667 cm -1 ; 1 H NM R(300 MHz, DMSO): δ 1.17-
1.21(d, 6H, 2 × i prCH 3 ), 1.27-1.89 (m, 10H,CH 2 ), 2.48 (s, 6H, SCH 3 ), 2.54 (s, 3H,
CH3), 3.79 (m, 1H, CH), 4.10-4.18 (m, 1H, i prCH), 7.09-7.19 (dd, 1H, Ar-H), 7.53-
7.56 (d, 2H, Ar-H, J=8.1Hz), 8.21-8.23 (d, 1H, CONH), 11.94 (s, 1H, CONH); MS
(m/z): 512 (M + ); Anal. Calcd for C 26 H 33 N 5 O 2 S 2 : C, 61.03; H, 6.50; N, 13.69; Found:
C, 61.05; H, 6.53; N, 13.66.
N 6 -(3-chlorophenyl)-N 3 -cyclohexyl-7-isopropyl-2,5-bis(methylthio)pyrazolo[1,5-
a] pyrimidine-3,6-dicarboxamide 10j. White solid; mp >320
° C, R f 0.44
(9:1Chloroform: Methanol); IR (KBr): 3198, 3157, 3042, 2942, 2832, 1734, 1668,
1654, 1257, 832, 806, 742 cm -1 ; MS (m/z): 532 (M + ); Anal. Calcd for
C 25 H 30 ClN 5 O 2 S 2 : C, 56.43; H, 5.68; N, 13.16; Found: C, 56.45; H, 5.67; N, 13.16.
N 6 -(3-chloro-4-fluorophenyl)-N 3 -cyclohexyl-7-isopropyl-2,5-bis(methylthio)
pyrazolo[1,5-a]pyrimidine-3,6-dicarboxamide 10k. Creamish solid; mp >320 ° C, R f
0.41 (9:1Chloroform: Methanol); IR (KBr): 3398, 3227, 3150, 2902, 2865, 1651,
1516, 1452, 1326, 880, 828, 750, 697 cm -1 ; 1 H NMR(300 MHz, DMSO):
Department of Chemistry, Saurashtra university, Rajkot-360005 143