Triethylamine → HCID 22160572, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (from Description 1a) (3.3 g, 14.0 mmol), 3-benzyloxy-2-benzyloxymethylprop-1-oxyamine (4.2 g, 14.0 mmol), triethylamine (5.8 ml, 41.6 mmol) and dioxan (100 ml) was stirred at 100° C. for 2.5 hours. The cooled reaction mixture was filtered and the precipitate collected and washed with dioxan (2×25 ml). The filtrate and washings were combined and evaporated to a syrup. Column chromatography on silica gel (eluted with chloroform-ethanol, 50:1) afforded the title compound (4.9 g, 70%). IR: υmax (KBr) 3240, 2910, 2860, 1690, 1585, 1565, 1475, 1420 cm-1. 1H NMR: δH [(CD3)2SO] 2.29 (1H, quintet, J=6.0, 5.6 Hz, CH), 3.56 (4H, d, J=5.6 Hz, 2×CH2OCH2Ph), 3.94 (2H, d, J=6.0 Hz, CH2ON) 4.46 (4H, s, 2×CH2Ph), 7.30 (10H, m, 2 ×Ph), 9.28 (1H, br.s, NCHO), 9.42 (1H, br.s, NCHO), 10.86 (2H, br.s, D2O exchangeable, 2×NHCHO).

Provenance & Evidence