Sodium cyanoborohydride → HCID 86651324, compound

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Reaction Steps

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.

Provenance & Evidence