Ethyl formate → HCID 21941886, compound

Participants

Reaction Steps

To a solution of (5-bromo-2-chloro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-amine (30 g, 108 mmol) in THF (500 ml) is added n-butyllithium (1.6 mol/l in n-hexane, 148 ml, 237 mmol) dropwise at −78° C. and the mixture is stirred for 10 min. Ethylformate (19 ml, 230 mol) is added dropwise to the mixture at −78° C., and the reaction mixture is allowed to warm to ambient temperature. After being stirred for 1 hour, the reaction mixture is quenched with saturated NH4Cl at −78° C. and then extracted with AcOEt. The combined extracts are washed with water, brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent:n-hexane:AcOEt=4:1) give 2-chloro-4-(2,2-dimethyl-propylamino)-pyrimidine-5-carbaldehyde. Rf=0.56 (n-hexane:AcOEt=1:1). 1H NMR (400 MHz, DMSO-d6) δ 1.00 (s, 9H), 3.41 (d, 2H), 8.40 (s, 1H), 8.88 (brs, 1H), 9.84 (s, 1H).

Provenance & Evidence