Triethylamine → HCID 14814216, compound

Participants

Reaction Steps

A solution of 4,6-dichloro-2,5-diformamidopyrimidine (3.27 g, 13.9 mmol), 1,4-bis(4-methoxybenzyloxy)but-2-oxyamine (5.06 g, 14 mmol) and triethylamine (5.88 ml, 42 mmol) in dioxan (100 ml) was heated at 100° C. for 90 minutes. The solution was allowed to cool, filtered and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1) to afford 6-[1,4-bis (4-methoxybenzyloxy)but-2-oxyamino]-4-chloro-2,5-diformamidopyrimidine as a pale yellow foam. 1H NMR: δH (CDCl3) 1.88 (2H, m, 3-H), 3.54 (4H, m, 1'-H and 4'-H), 3.73 (3H, s, CH3), 3.74 (3H, s, CH3), 4.07 (1H, m, 2'-H), 4.37 (4H, m, 2×ArCH2), 6.88 (4H, m, ArH), 7.21 (4H, m, ArH), 9.17, 9.27, 9.30, 9.43 (total 2H, 4×s, D2O exchange leaves s at 9.27, 2×HCO), 10.67 (1H, br.s, D2O exchangeable, NH) and 10.85 (1H, br.s, D2O exchangeable, NH).

Provenance & Evidence