Methanol → HCID 178445464, compound

Participants

Reaction Conditions

Reaction Steps

3.1 g (13.0 mMol) hexanoic acid 4-methoxy-pyrimidin-2-ylmethyl ester and 5.85 g (39 mMol) NaI are dissolved in 130 ml (13 mMol) of a 0.1 M solution of water in acetonitrile at 60° C. Then 4.95 ml (39 mMol) Me3SiCl are added via syringe. The resulting suspension is stirred for 7 h at 60° C. and then cooled to rt again. Then 15 ml of MeOH are added dropwise. After stirring for 10 additional minutes, the reddish suspension is concentrated in vacuo. The residue is redissolved in 300 ml EtOAc and 100 ml sat. NaHCO3 solution, the aq. layer separated off and extracted with 2×300 ml EtOAc. The organic phases are washed with 50 ml of a 0.5 M solution of Na2S2O3 and brine, dried (Na2SO4) and concentrated. Crystallization from CH2Cl2 and hexane gives the title compound: m.p.: 78° C.; MS: [M+1]+=225.

Provenance & Evidence