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Chapter 4
Synthesis of highly substituted pyrazolopyrimidine
MS (m/z): 484 (M + ); Anal. Calcd for C 24 H 29 N 5 O 2 S 2 : C, 59.60; H, 6.04; N, 14.48;
Found: C, 59.56; H, 6.03; N, 14.45.
N 6 -(3-chlorophenyl)-N 3 -cyclohexyl-7-methyl-2,5-bis(methylthio)pyrazolo[1,5-a]
pyrimidine-3,6-dicarboxamide 10b. Creamish solid; mp >320
o C, R f 0.40
(9:1Chloroform : Methanol); IR (KBr): 3379, 3024, 2902, 1651, 1516,1483, 1332,
845, 800, 756, 695 cm -1 ; 1 H NMR (300 MHz, DMSO): δ 1.35-1.81 (m, 10H,CH 2 ),
2.45 (s, 6H, SCH 3 ), 2.70 (s, 3H, CH3), 3.79 (m, 1H, CH), 7.05 (s, 1H, Ar-H), 7.31-
7.35 (m, 2H, Ar-H), 8.0 (s, 1H, AR-H), 8.56 (s, 1H, CONH), 12.56 (s, 1H, CONH);
13 C NMR (100 MHz, DMSO): 12.40, 23.86, 25.34, 27.54, 30.54, 32.55, 45.86, 98.23,
98.89, 117.29, 118.69, 121.70, 129.88, 133.31, 141.26, 148.07, 154.00, 158.20,
161.85, 163.79, 165.67; MS (m/z): 503 (M + ); Anal. Calcd for C 23 H 26 ClN 5 O 2 S 2 : C,
54.80; H, 5.20; N, 13.89; Found: C, 54.81; H, 5.24; N, 13.89.
N 6 -(3-chloro-4-fluorophenyl)-N 3 -cyclohexyl-7-methyl-2,5-bis(methylthio)
pyrazolo[1,5-a]pyrimidine-3,6-dicarboxamide 10c. White solid; mp >320 ° C, R f
0.48 (9:1Chloroform: Methanol); IR (KBr): 3323, 3026, 2908, 2856, 1674, 1630,
1563, 1473, 1246, 927, 843, 798, 732, cm -1 ; MS (m/z): 522 (M + ); Anal. Calcd for
C 23 H 25 ClFN 5 O 2 S 2 : C, 52.91; H, 4.83; N, 13.41; Found: C, 52.96; H, 4.83; N, 13.45.
N 6 -(4-chlorophenyl)-N 3 -cyclohexyl-7-methyl-2,5-bis(methylthio)pyrazolo[1,5-a]
pyrimidine-3,6-dicarboxamide 10d. Creamish solid; mp >320
° C, R f 0.35
(9:1Chloroform: Methanol); IR (KBr): 3379, 3024, 2902, 1651, 1516, 1483, 1332,
1166, 954, 852, 822, 748, 709 cm -1 ; MS (m/z): 503 (M + ); Anal. Calcd for
C 23 H 26 ClN 5 O 2 S 2 : C, 54.80; H, 5.20; N, 13.89; Found: C, 54.81; H, 5.24; N, 13.89.
N 3 -cyclohexyl-N 6 -(4-fluorophenyl)-7-methyl-2,5-bis(methylthio)pyrazolo[1,5-a]
pyrimidine-3,6-dicarboxamide 10e. White solid; mp >320
° C, R f 0.28
(9:1Chloroform: Methanol); IR (KBr): 3430, 3133, 3051, 2922, 1651, 1516, 1483,
1232, 1166, 954, 883, 780, 743, 698 cm -1 ; MS (m/z): 487 (M + ); Anal. Calcd for
C 23 H 26 FN 5 O 2 S 2 : C, 56.65; H, 5.37; N, 14.36; Found: C, 56.61; H, 5.34; N, 14.39.
N 3 -cyclohexyl-7-methyl-2,5-bis(methylthio)-N 6 -(4-nitrophenyl)pyrazolo[1,5-a]
pyrimidine-3,6-dicarboxamide 10f. Yellow solid; mp >320 ° C, R f 0.29 (9:1
Chloroform: Methanol); IR (KBr): 3421, 3122, 3088, 2922, 1651, 1516, 1483, 1232,
Department of Chemistry, Saurashtra university, Rajkot-360005 142