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Chapter 4
Synthesis of highly substituted pyrazolopyrimidine
N 3 -cyclohexyl-7-isopropyl-N 6 -(2,5-dimethylphenyl)-2,5-bis(methylthio)pyrazolo
[1,5-a]pyrimidine-3,6-dicarboxamide 10p. White solid; mp >320 ° C, R f 0.22
(9:1Chloroform: Methanol); IR (KBr): 3503, 3450, 3206, 3068, 2908, 1628, 1548,
1420, 1342, 1066, 825, 754 cm -1 ; MS (m/z): 525 (M + ); Anal. Calcd for C 27 H 35 N 5 O 3 S 2 :
C, 61.68; H, 6.71; N, 13.32; Found: C, 61.67; H, 6.72; N, 13.36.
N 3 -cyclohexyl-7-cyclopropyl-2,5-bis(methylthio)-N 6 -p-tolylpyrazolo[1,5-a]pyrimidine-3,6-dicarboxamide
10q. Creamish solid; mp >320 ° C, R f 0.35 (9:1Chloroform:
Methanol); IR (KBr): 3460, 3226, 3047, 2938, 1615, 1539, 1422, 1336, 1066, 834,
757 cm -1 ; 1 H NMR (300 MHz, DMSO): δ 0.98-1.01 (m, 4H, 2 ×CH 2 ), 1.16-1.37 (m,
4H, CH 2 ), 1.55-1.89 (m, 6H, CH 2 ), 2.25-2.27 (s, 3H, CH 3 ), 2.43.2.77 (m, 6H, SCH 3 ),
3.64 (m, 2H, CH), 7.09-7.19 (dd, 2H, Ar-H, J=7.8Hz, J=8.4Hz), 7.67-7.70 (d, 1H,
Ar-H, J=8.1Hz), 8.21-8.23 (d, 1H, CONH), 11.96 (s, 1H, CONH); MS (m/z): 509
(M + ); Anal. Calcd for C 26 H 31 N 5 O 2 S 2 : C, 61.27; H, 6.13; N, 13.74; Found: C, 61.25; H,
6.17; N, 13.76.
N 6 -(3-chlorophenyl)-N 3 -cyclohexyl-7-cyclopropyl-2,5-bis(methylthio)pyrazolo
[1,5-a]pyrimidine-3,6-dicarboxamide 10r. White solid; mp >320 ° C, R f 0.43
(9:1Chloroform: Methanol); IR (KBr): 3457, 3345, 3147, 3038, 2952, 1615, 1539,
1422, 1336, 1076, 828, 745 cm -1 ; MS (m/z): 530 (M + ); Anal. Calcd for
C 25 H 28 ClN 5 O 2 S 2 : C, 56.64; H, 5.32; N, 13.21; Found: C, 56.62; H, 5.32; N, 13.24.
N 6 -(3-chloro-4-fluorophenyl)-N 3 -cyclohexyl-7-cyclopropyl-2,5-bis(methylthio)
pyrazolo[1,5-a]pyrimidine-3,6-dicarboxamide 10s. Creamish solid; mp >320 ° C, R f
0.40 (9:1Chloroform: Methanol); IR (KBr): 3448, 3250, 3130, 2948, 2902, 1651,
1516, 1483, 1332, 1166, 850, 772, 705 cm -1 ; MS (m/z): 548 (M + ); Anal. Calcd for
C 25 H 27 ClFN 5 O 2 S 2 : C, 54.78; H, 4.97; N, 12.78; Found: C, 54.76; H, 4.95; N, 12.74.
N 6 -(4-chlorophenyl)-N 3 -cyclohexyl-7-cyclopropyl-2,5-bis(methylthio)pyrazolo
[1,5-a]pyrimidine-3,6-dicarboxamide 10t. Creamish solid; mp >320 ° C, R f 0.46
(9:1Chloroform: Methanol); IR (KBr): 3328, 3248, 3057, 2964, 2926, 1651, 1516,
1483, 1328, 1158, 850, 772 cm -1 ; MS (m/z): 530 (M + ); Anal. Calcd for
C 25 H 28 ClN 5 O 2 S 2 : C, 56.64; H, 5.32; N, 13.21; Found: C, 56.62; H, 5.32; N, 13.24.
Department of Chemistry, Saurashtra university, Rajkot-360005 145