Methylamine → HCID 58739054, compound

Participants

Reaction Steps

A solution of 2-methanesulfonyl-5-benzyloxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (1.180 g, 3.22 mmol) in acetonitrile (20 ml) was treated at 25° C. with N,N-diisopropylethylamine (1.5 ml, 0.87 mmol) followed by 4.8 ml (9.6 mmol) of a 2M solution of methylamine in tetrahydrofuran. After 30 min, the solvent was evaporated in vacuo and the residue was chromatographed on silica gel (elution toluene-ethyl acetate, 25:75) to give 0.838 g (82% yield) of the title ester as a clear syrup. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.30 (3H, t, J=7.1 Hz, CH3), 3.04 (3H, d, J=5.1 Hz, NCH3), 3.42 (3H, s, NCH3), 4.32 (2H, q, J=7.1 Hz, OCH2), 4.58 (1H, broad q, NH), 5.07 (2H, s, OCH2), 7.3–7.37 (3H, m, aromatics), 7.47 (2H, m, aromatics). HRMS (FAB POS) calculated for C16H20N3O4 [M+H+]: 318.145381. found: 318.144860.

Provenance & Evidence