تفاعل #47755

معادلة التفاعل

Chloroform

K2CO3

Compound 27

5-Acetylamino-7-isopropoxy-3-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one

THF

→

5-Amino-7-isopropoxy-3-β-D-ribofuranosyl-thiazolo[4,5-d]pyrimidin-2-one

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture was concentrated under vacuum
2. 2
   أخرىpurified by flash column chromatography (3% methanol in chloroform)
3. 3
   أخرىThe isolated solid was triturated with ethyl ether yielding 210 mg (51%) of pure 28 as a white solid

الإجراء التجريبي

Compound 27 (600 mg, 1.14 mmol) was dissolved in methanol (15 ml) under a dry nitrogen atmosphere. K2CO3 (31.5 mg, 0.2 mmol) was added and the mixture was stirred for 18 h periodically being monitored by TLC (1:1 THF:Chloroform). The reaction mixture was concentrated under vacuum and purified by flash column chromatography (3% methanol in chloroform). The isolated solid was triturated with ethyl ether yielding 210 mg (51%) of pure 28 as a white solid: 1H NMR (400 MHz, d6-DMSO) δ 6.83 (s, 2H), 5.86 (d, J=5.2 Hz, 1H), 5.34 (m, 1H), 5.26 (d, J=5.6 Hz, 2H), 4.95 (d, J=5.6 Hz, 1H), 4.77 (m, 1H), 4.67 (m, 1H), 4.09 (m, 1H), 3.75 (m, 1H), 3.58 (m, 1H), 3.43 (m, 1H), 1.29 (d, J=6.4 Hz, 6H); MS (+)-ES [M+H]+ m/z 359, [2M+H]+ m/z 717.3. Rf=0.2 (50% THF—CHCl3). Elemental analysis for C13H18N4O16S: calc'd: C, 43.57; H, 5.06; N, 15.63; S, 8.95. Found: C, 43.39; H, 5.07; N, 15.45; S, 8.82.

المصدر