Reaction #2146753

Reaction equation

(2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(4-methylbenzoyloxy)-5-(4-methylbenzoyloxymethyl)-3-ethynyl-tetrahydro-furan-3-ol

sodium methoxide

HCl

→

(2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-hydroxymethyl-tetrahydrofuran-3,4-diol

Solvents

CH2Cl2

MeOH

methanol

Conditions

Workup

1. 1
   Otherevaporated under vacuum
2. 2
   Otherto dry
3. 3
   Otherpurified by flash chromatography (CH2Cl2:MeOH=92:8)

Procedure

Crude intermediate (2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(4-methylbenzoyloxy)-5-(4-methylbenzoyloxymethyl)-3-ethynyl-tetrahydro-furan-3-ol (434 mg, 0.74 mmol) is dissolved in MeOH (5 ml) and CH2Cl2 (5 ml). 30% sodium methoxide in methanol solution (1.38 ml, 7.4 mmol, 10 equiv.) is added and the mixture is stirred at room temperature for 15 mins. The mixture is neutralized to pH 7.0 by addition of 1N HCl solution and evaporated under vacuum to dry, purified by flash chromatography (CH2Cl2:MeOH=92:8) to yield (2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-hydroxymethyl-tetrahydrofuran-3,4-diol. 1H-NMR (CDCl3): δ 8.58 (s, 1H), 8.00 (d, 1H, J=3.9 Hz), 6.68 (d, 1H, J=3.9 Hz), 6.49 (s, 1H), 4.51 (d, 1H, J=9.0 Hz), 4.20-3.75 (m, 3H), 2.51 (s, 1H). ESI-MS: calcd. for C13H12ClN3O4 (309.05). found: 310.3.

Source