1
2
G. ELGEMEIE ET AL.
1
region); yellow solid; (EtOH); yield (89%); mp154°C; H-NMR (500 MHz, CDCl ):
3
ꢀ
ꢀ
δ 2.03–2.11 (4s, 12H, 4xOAc), 4.11 (m, 2H, 2H-6 ), 4.29–4.30 (m, 1H, H-5 ),
ꢀ
ꢀ
ꢀ
5
1
(
(
(
(
.15 (t, 1H, H-4 ), 5.23 (t, 1H, H-3 ), 5.31 (t, 1H, H-2 ), 5.74–5.76 (d, 1H, J
0.70 Hz, H-1 ), 6.73 (brs, 2H, NH ), 8.34 (s, 1H, pyrazole H-2); C NMR: δ 21.25
4CH CO), 62.54 (C-6 ), 68.22 (C-4 ), 71.44 (C-2 ), 73.32 (C-3 ), 77.42 (C-5 ), 81.22
C-1 ), 92.25 (C-6), 93.12 (C-3), 116.33 (CN), 117.24 (CN), 132.52 (C-3 ), 155.44
C-2), 160.46 (C-5), 170.66 (4CO), 172.22 (C-6). Anal. Calcd. For C H N O S
ꢀ
ꢀ
1
–2 =
ꢀ
13
2
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
3
ꢀ
a
22
22
6
9
546.51): C, 48.35; H, 4.06; N, 15.38; S, 5.87%. Found: C, 48.45; H, 4.16; N, 15.40; S,
5.85%.
ꢀ
ꢀ
ꢀ
ꢀ
3
.1.2.8. 2,5-Diamino-7-(2 ,3 ,4 ,6 -tetra-O-acetyl-β-D-galactopyranosylthio)-3–
(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile(5h). Compound 5h
was purified by column chromatography (petroleum. ether/ethyl acetate 8:2,R =
f
1
−
0
.45–47 region); yellow solid; (EtOH); yield (80%); mp172°C; IR (KBr, cm )υ
1
3
470, 3436, 3029, 2207, 1743, 1596; H-NMR (500 MHz, DMSO-d ): δ 1.94–2.19
6
ꢀ
ꢀ
ꢀ
(4s, 12H, 4xOAc), 4.06–4.15 (m, 3H,2H-6 and H-5 ), 4.94–4.97 (t, 1H, H-4 ), 5.28–
ꢀ
ꢀ
ꢀ
5.38 (m, 2H, H-3 and H-2 ), 5.52–5.54 (d, 1H, J
ꢀ
ꢀ
10.3 Hz, H-1 ), 6.10 (s, 2H,
1
–2 =
NH ), 6.43 (s, 2H, NH ), 7.37–7.89 (m, 5H, C H ). Anal. Calcd. For C H N O S
2
2
6
5
27 28
8
9
(
5
640.62): C, 50.62; H, 4.41; N, 17.49; S, 5.01%. Found: C, 50.50; H, 4.35; N, 17.37; S,
.11%.
ꢀ
ꢀ
ꢀ
ꢀ
3
.1.2.9. 2,5-Diamino-3-((4-methoxyphenyl)diazenyl)-7-(2 ,3 ,4 ,6 -tetra-O-
acetyl-β-D-galactopyranosylthio)-pyrazolo[1,5-a]pyrimidine-6-carbonitrile(5i).
Compound 5i was purified by column chromatography (petroleum. ether/ethyl
acetate 8:2,R = 0.62–64 region); yellow solid; (EtOH); yield (85%); mp201°C;
f
1
H-NMR (500 MHz, DMSO-d ): δ 1.92–2.10 (4s, 12H, 4xOAc), 3.41 (s, 3H,
OCH ), 3.98–4.10 (m, 2H, 2H-6 ), 4.11–4.12 (m, 1H, H-5 ), 4.92–4.94 (t, 1H, H-4 ),
.11–5.13 (t, 1H, H-3 ), 5.38 (t, 1H, H-2 ), 5.79–5.81 (d, 1H, J
.35 (s, 2H, NH ), 6.64 (s, 2H, NH ), 7.31–7.54 (m, 4H, C H ); C NMR: δ 20.17
4CH CO), 62.12 (C-6 ), 68.62 (C-4 ), 70.31 (C-2 ), 73.32 (C-3 ), 76.32 (C-5 ), 82.21
C-1 ), 89.41 (C-6), 90.21 (C-3), 115.45 (2C, Ar-C), 117.11 (CN), 123.51 (Ar-C),
27.68 (2C, Ar-C), 134.52 (C-3 ), 158.10 (C-2), 167.68 (C-5), 169.82 (4CO), 171.17
6
ꢀ
ꢀ
ꢀ
ꢀ
3
ꢀ
ꢀ
5
6
(
(
ꢀ
ꢀ
10.7 Hz, H-1 ),
1
–2 =
1
3
2
2
ꢀ
6
4
ꢀ
ꢀ
ꢀ
ꢀ
3
ꢀ
a
1
(
4
C-6). Anal. Calcd. For C H N O S (670.65): C, 50.15; H, 4.51; N, 16.17; S,
.78%. Found: C, 50.35; H, 4.45; N, 16.78; S, 4.62%.
28 30 8 10
ꢀ
ꢀ
ꢀ
ꢀ
3
.1.2.10. 2,5-Diamino-7-(2 ,3 ,4 ,6 -tetra-O-acetyl-β-D-galactopyranosylthio)-3-
(
p-tolyldiazenyl)pyrazolo [1,5-a]pyrimidine-6-carbonitrile(5j). Compound 5j
was purified by column chromatography (petroleum ether/ethyl acetate 8:2,R =
f
1
0
.61–63 region); yellow solid; (EtOH); yield (82%); mp186°C; H-NMR (500 MHz,
DMSO-d )δ 2.05–2.09 (4s, 12H, 4xOAc), 2.69–2.70 (s, 3H, CH ), 4.12 (m, 1H,
6
3
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
H-5 ), 4.23 (t, 1H, H-4 ), 4.33–4.40 (m, 2H, 2H-6 ), 4.67 (t,1H, H-3 ), 5.23 (t, 1H,
H-2 ), 5.55–5.56 (d, 1H, J1
ꢀ
ꢀ
ꢀ
3.8 Hz, H-1 ), 6.53 (s, 2H, NH ), 6.65 (s, 2H, NH ),
–2 =
2
2