Triethylamine → Tert-butyl 2-(2-aminopyrimidin-4-ylamino)ethylcarbamate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 2-aminoethylcarbamate (3.27 g, 20.4 mmol) and 2-amino-6-chloropyrimidine (2.38 g, 18.4 mmol) were combined in 2-methoxyethanol with triethylamine (4.3 mL, 30.3 mmol) and heated to 130° C. overnight. The mixture was diluted with methylene chloride and washed with 1 N sodium hydroxide. The aqueous layer was extracted with methylene chloride followed by ethyl acetate. The organic layers were combined, absorbed on silica gel, and purified using silica gel chromatography, eluting with a gradient of methanol in methylene chloride (1-12%) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.44 (s, 9H) 3.32 (q, J=5.31 Hz, 2H) 3.38-3.50 (m, 2H) 4.70 (s, 2H) 4.91-5.19 (m, 2H) 5.78 (d, J=5.76 Hz, 1H) 7.81 (d, J=5.76 Hz, 1H); MS (ESI+) m/z 253.9 (M+H)+.

Provenance & Evidence