Potassium Sodium Tartrate → 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanal

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanoate (1.6 g, 4.1 mmol) was dissolved in THF (30 mL) and cooled to −78° C. The reaction mixture was treated with a 1.0M solution of lithium tetrahydroaluminate in THF (8.6 mL) and stirred at −78° C. for 1 hr. A saturated solution of NH4Cl was added and the mixture was diluted with DCM. The reaction mixture was treated with a saturated solution of Rochelle's salt and stirred on high at ambient temperature for 1 hr. The layers were separated and the aqueous phase was extracted into DCM/MeOH (3×), dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanal as a white foam (900 mg, 62%). LC/MS (ESI+): m/z 384 (M+H)

Provenance & Evidence