Sodium cyanoborohydride → HCID 86651324, compound

HRID 390069Notes

Reaction equation

HRID 390069 reaction equation
Cl.[NH2:2][C:3]([CH2:8][S:9][CH3:10])([CH2:6][OH:7])[CH2:4][OH:5].[CH2:11]([O:18][CH2:19][N:20]1[C:28]2[C:27]([Cl:29])=[N:26][CH:25]=[N:24][C:23]=2[C:22]([CH:30]=O)=[CH:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([BH3-])#N.[Na+]>CO>[CH2:11]([O:18][CH2:19][N:20]1[C:28]2[C:27]([Cl:29])=[N:26][CH:25]=[N:24][C:23]=2[C:22]([CH2:30][NH:2][C:3]([CH2:8][S:9][CH3:10])([CH2:6][OH:7])[CH2:4][OH:5])=[CH:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 58158418HCID 58158418, compoundHCID 131730259HCID 131730259, compound

Product 1

HCID 86651324HCID 86651324, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-2-(methylthiomethyl)propane-1,3-diol, hydrochloride salt (60.0 mg, 0.397 mmol) and 5-(benzyloxymethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde (126 mg, 0.397 mmol) in methanol (4 mL) was added sodium cyanoborohydride (27.4 mg, 0.436 mmol). After 15 h at ambient temperature the contents of the flask were concentrated under reduced pressure. Purification by flash column chromatography (CH2Cl2:7 M methanolic ammonia, 10:1) gave 2-((5-(benzyloxymethyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(methylthiomethyl)propane-1,3-diol (110 mg, 0.252 mmol, 64%) as a yellow gum. 1H NMR (CD3OD) δ 8.57 (s, 1H), 7.84 (s, 1H), 7.18-7.13 (m, 5H), 5.82 (s, 2H), 4.52 (s, 2H), 3.95 (s, 2H), 3.68 (d, J=11.5 Hz, 2H), 3.61 (d, J=11.5 Hz, 2H), 2.76 (s, 2H), 2.11 (s, 3H). +ESMS Found 437.1407 (M+H+) C20H26N4O3SCl requires 437.1414.

Workup

  1. concentrationAfter 15 h at ambient temperature the contents of the flask were concentrated under reduced pressure
  2. customPurification by flash column chromatography (CH2Cl2:7 M methanolic ammonia, 10:1)

Sources & evidence

ORD record
ord-caf6ae52cb124442a72da8f6023dc6d6
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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