반응 #1105216

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compound ( 23 )

4-Amino-7-[2-deoxy-β-D-erythropentofuranosyl]-5-trimethylsilylethynyl-7H-pyrrolo[2,3-d]pyrimidine

K2CO3

→

crystals

수율 73.0%

4-Amino-7-[2-deoxy-β-D-erythropentofuranosyl]-5-ethynyl-7H-pyrrolo[2,3-d]pyrimidine

수율 73.0%

용매

MeOH

반응 조건

후처리

1. 1
   기타results in hydrolysis after 1 h
2. 2
   기타After the solution has been subjected to rotary evaporation
3. 3
   기타the residue is chromatographed on silica gel in the eluent methylene chloride/MeOH (8:1)
4. 4
   기타Recrystallization from MeOH

실험 절차

200 mg of compound (23) are dissolved in 20 ml of MeOH. Adding 8 mg of K2CO3 results in hydrolysis after 1 h of stirring. After the solution has been subjected to rotary evaporation, the residue is chromatographed on silica gel in the eluent methylene chloride/MeOH (8:1). Recrystallization from MeOH results in colorless crystals (73%). Calc. C 56.93, H 5.15, N 20.43; found C 56.77, H 5.71, N 20.42. 1H-NMR (DMSO): 8.13 (s, 1H, H-2), 7.81 (s, 1H, H-6), 6.65 (broad, 2H, NH2), 6.49 (t, 1H, H-1′), 5.25 (m, 1H, 3′-OH), 5.05 (m, 1H, 5′-OH), 4.36 (m, 1H, H-3′), 4.26 (s, 1H, ethyne), 3.84 (s, 1H, H-4′), 3.56 (m, 2H, H-5′), 2.47 (m, 1H, H-2′), 2.21 (m, 1H, H-2′).

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