Formamide → HCID 178435582, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-amino-5-ethylcyclopent-1-enecarboxylate (1.62 g, 9.57 mmol) was combined with ammonium formate (3.02 g, 47.9 mmol) and formamide (3.80 mL, 95.7 mmol), and the reaction mixture was heated to 150° C. for 16 hours. Conversion was confirmed by LCMS. The reaction was cooled to room temperature and partitioned between a 5:1 DCM/i-PrOH solution and water. The aqueous layer was extracted multiple times with the same DCM/i-PrOH solution. The combined extracts were concentrated to dryness and partitioned between DCM and brine. The organic portion was concentrated to provide 5-ethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (1.13 g, 6.88 mmol, 71.9% yield) as an oil, which was taken to the next step without purification. MS (APCI+) [M+H]: 165.0.

Provenance & Evidence