Hydrochloric Acid → HCID 89630068, compound

Participants

Reaction Conditions

Reaction Steps

To 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (135 mg, 0.339 mmol), tosmic (73 mg, 0.37 mmol) and potassium hydroxide (38 mg, 0.68 mmol), was added methanol (10 mL). The resulting solution was stirred for 12 hours at 25° C. and then the pH was adjusted to pH=6 with hydrogen chloride (1M aqueous solution). The reaction was extracted with ethyl acetate (×3) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography using silica gel, eluting with 25% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford 5-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)oxazole as a yellow oil. LRMS (ESI) calc'd for C21H24N5O4Si [M+H]+: 438, found 438.

Provenance & Evidence