Methanol → 4-[[(Diisopropylamino)methylene]amino]-3-pyridinol N,N-dimethyl carbamate

Participants

Reaction Steps

To a stirred mixture of 4-[[(diisopropylamino)methylene]amino]-3-pyridinol (1.06 g) and triethylamine (1.0 ml) in 25 ml dry Et2O was added dimethyl carbamyl chloride (0.53 ml). The mixture was stirred at room temperature for 2 hours, after which no starting material remained as seen by TLC (silica, 10:90 CH3OH:CH2Cl2). The mixture was diluted with 25 ml Et2O, filtered, washed with Et2O, and the filtrate concentrated in vacuo and chromatography on silica using EtOAc eluent. The fractions containing desired product were combined and concentrated to provide 500 mg of pure product. Another run was carried out in the same manner as above using 740 mg of starting material. The products from both runs were combined. Recrystallization attempts failed, and the product was dried in vacuo to provide 790 mg of a white solid, m.p. 76°-79° C.

Provenance & Evidence