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Chapter 4
Synthesis of highly substituted pyrazolopyrimidine
δ 1.27-1.30 (d, 6H, 2 × i prCH 3 ), 1.34-1.89 (m, 10H,CH 2 ), 2.49 (s, 6H, SCH 3 ), 3.74 (m,
1H, CH), 4.10-4.18 (m, 1H, i prCH), 7.31-7.37 (m, 1H, Ar-H), 7.43-7.46 (m, 1H, Ar-
H), 8.10-8.12 (m, 1H, Ar-H), 8.54-8.57 (d, 1H, CONH), 12.02(s, 1H, CONH); MS
(m/z): 550 (M + ); Anal. Calcd for C 25 H 29 ClFN 5 O 2 S 2 : C, 54.58; H, 5.31; N, 12.73;
Found: C, 54.59; H, 5.33; N, 12.76.
N 6 -(4-chlorophenyl)-N 3 -cyclohexyl-7-isopropyl-2,5-bis(methylthio)pyrazolo[1,5-
a]pyrimidine-3,6-dicarboxamide 10l. White solid; mp >320
° C, R f 0.38
(9:1Chloroform: Methanol); IR (KBr): 3425, 3258, 3124, 2998, 2847, 1661, 1532,
1425, 1318, 867, 817, 753, 689 cm -1 ; 1 H NMR (300 MHz, DMSO): δ 1.17-1.19(d,
6H, 2 × i prCH 3 ), 1.27-1.38 (m, 4H,CH 2 ), 1.66-1.89 (m, 6H,CH 2 ), 2.48 (s, 6H, SCH 3 ),
3.79 (m, 1H, CH), 4.10-4.18 (m, 1H, i prCH), 7.32-7.35 (d, 2H, Ar-H, J=8.1Hz), 7.67-
7.70 (d, 1H, Ar-H, J=8.4Hz), 8.53-8.57 (d, 1H, CONH), 11.96(s, 1H, CONH); 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 3 -cyclohexyl-N 6 -(4-fluorophenyl)-7-isopropyl-2,5-bis(methylthio)pyrazolo[1,5-
a]pyrimidine-3,6-dicarboxamide 10m. Creamish solid; mp >320 ° C, R f 0.45 (9:1
Chloroform: Methanol); IR (KBr): 3454, 3260, 3142, 2978, 2850, 1645, 1542, 1425,
1318, 867, 750 cm -1 ; MS (m/z): 515 (M + ); Anal. Calcd for C 25 H 30 FN 5 O 2 S 2 : C, 58.23;
H, 5.86; N, 13.58; Found: C, 58.25; H, 5.87; N, 13.56.
N 3 -cyclohexyl-7-isopropyl-2,5-bis(methylthio)-N 6 -(4-nitrophenyl)pyrazolo[1,5-
a]pyrimidine-3,6-dicarboxamide 10n. Creamishsolid; mp >320 ° C, R f 0.34
(9:1Chloroform: Methanol); IR (KBr): 3460, 3367, 3242, 2956, 2845, 1647, 1538,
1420, 1318, 867, 750, 700 cm -1 ; MS (m/z): 542 (M + ); Anal. Calcd for C 25 H 30 N 6 O 4 S 2 :
C, 55.33; H, 5.57; N, 15.49; Found: C, 55.35; H, 5.57; N, 15.46.
N 3 -cyclohexyl-7-isopropyl-N 6 -(4-methoxyphenyl)-2,5-bis(methylthio)pyrazolo
[1,5-a]pyrimidine-3,6-dicarboxamide. 10o. White solid; mp >320 ° C, R f 0.23
(9:1Chloroform: Methanol); IR (KBr): 3483, 3242, 3162, 3068, 2902, 1675, 1584,
1425, 1332, 1066, 954, 820, 750 cm -1 ; MS (m/z): 528 (M + ); Anal. Calcd for
C 26 H 33 N 5 O 3 S 2 : C, 59.18; H, 6.30; N, 13.27; Found: C, 59.20; H, 6.32; N, 13.26.
Department of Chemistry, Saurashtra university, Rajkot-360005 144