Lithium Chloride → 5-(4-(Hydroxymethyl)thiazol-2-yl)-1,3-dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Participants

Reaction Steps

Sodium borohydride (0.856 g, 22.62 mmol) was added to a solution of ethyl 2-(1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thiazole-4-carboxylate (step 1) (5.254 g, 11.31 mmol) and lithium chloride (0.959 g, 22.62 mmol) in ethanol (145 ml) and THF (290 ml) at 0° C. The mixture was stirred at room temperature for 16 hours. Further portions of lithium chloride (0.959 g, 22.62 mmol) and sodium borohydride (0.856 g, 22.62 mmol) were added and the mixture stirred for a further 4 hours. The reaction was quenched with saturated NaHCO3 (aq) (250 ml), diluted with water (100 ml) and extracted with chloroform (3×350 ml). The combined organic extracts were washed with water (200 ml) and brine (2×200 ml), dried over sodium sulfate and evaporated under vacuum to afford the title compound.

Provenance & Evidence