Sodium cyanoborohydride → HCID 86651334, compound

HRID 390082Notes

Reaction equation

HRID 390082 reaction equation
C([BH3-])#N.[Na+].[CH3:5][NH:6][C@H:7]([C@@H:10]([OH:14])[CH2:11][S:12][CH3:13])[CH2:8][OH:9].[CH2:15]([O:22][CH2:23][N:24]1[C:32]2[C:31]([Cl:33])=[N:30][CH:29]=[N:28][C:27]=2[C:26]([CH:34]=O)=[CH:25]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[CH2:15]([O:22][CH2:23][N:24]1[C:32]2[C:31]([Cl:33])=[N:30][CH:29]=[N:28][C:27]=2[C:26]([CH2:34][N:6]([CH3:5])[C@@H:7]([C@H:10]([OH:14])[CH2:11][S:12][CH3:13])[CH2:8][OH:9])=[CH:25]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 58158418HCID 58158418, compoundHCID 86651335HCID 86651335, compound

Product 1

HCID 86651334HCID 86651334, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (68 mg, 1.1 mmol) was added to a stirred solution of (2S,3R)-2-(methylamino)-4-(methylthio)butane-1,3-diol (120 mg, 0.7 mmol) and 5-(benzyloxymethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde (263 mg, 0.9 mmol) in methanol (2 ml) and the resulting reaction left for 48 h. The reaction was concentrated in vacuo and the resulting residue purified by flash chromatography on silica gel eluting with 5% MeOH/DCM=>10% MeOH/DCM to afford, presumably, (2S,3R)-2-(((5-(benzyloxymethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)(methyl)amino)-4-(methylthio)butane-1,3-diol B.4 (220 mg, 67% yield) as a syrup which was used in the next step without purification.

Workup

  1. customthe resulting reaction
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe resulting residue purified by flash chromatography on silica gel eluting with 5% MeOH/DCM=>10% MeOH/DCM
  4. customto afford
  5. custompresumably, (2S,3R)-2-(((5-(benzyloxymethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)(methyl)amino)-4-(methylthio)butane-1,3-diol B.4 (220 mg, 67% yield) as a syrup which was used in the next step without purification

Sources & evidence

ORD record
ord-662543463ada4ff68276da899bc7157a
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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