Dimethylamine → tert-Butyl N-[1-(pyrimidin-2-yl)cyclopropyl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of (1-Carbamimidoyl-cyclopropyl)-carbamic acid tert-butyl ester hydrochloride (3.62 g, 15.4 mmol) in anhydrous EtOH (62 mL) was added dimethylaminoacrolein (3.6 mL, 36. mmol) and dimethylamine (2 M in THF, 10. mL, 20. mmol). The reaction was heated at 70° C. for 18 h. The EtOH was removed in vacuo and the residue was dissolved in EtOAc (150 mL) and washed with water (3×100 ml). The organic phase was dried with Na2SO4 and concentrated to give a red oil. The product was crystallized from the oil using warm hexanes (30 mL) and the light orange solids were collected by filtration. The filtrate was re-processed in the same manner two additional times. In total 2.23 g of the title compound was isolated as a light orange powder, m/z 236.40 [M+1]+

Provenance & Evidence