Formamide → 5-propan-2-yl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-amino-5-isopropylcyclopent-1-enecarboxylate (3.272 g, 17.86 mmol), ammonium formate (5.630 g, 89.28 mmol), and formamide (7.092 mL, 178.6 mmol) was heated at 150° C. for 20 hours. The reaction was diluted with water, and extracted with 1:5 IPA:DCM, until no more product in aqueous by TLC. The combined organics were concentrated under reduced pressure, dissolved in DCM and dried Na2SO4. The reaction was filtered and concentrated to give 5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (4.29 g, 100%), which was used without further purification. LCMS (APCI+) m/z 179.0 [M+H]+; Rt=2.33 min.

Provenance & Evidence