4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 849409, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (4.6 g, 19.6 mmol) in ethanol (90 mL) is added 5-amino-1,3-dimethylpyrazole (4.4 g, 39.2 mmol). The mixture is heated for 22 hours at 80° C. The reaction is cooled to room temp and concentrated in vacuo. The solid which remains is dissolved in CHCl3 and washed with aqueous saturated NaHCO3 solution. The organic phase is dried (MgSO4), filtered and concentrated in vacuo and the resulting residue is purified over silica (50% EtOAc//hexanes, followed by 100% EtOAc) to afford 4.8 g of the desired product: 1H NMR (300 MHz, CDCl3) δ10.29 (s, NH), 8.82 (s, 1H), 6.30 (s, 1H), 4.43 (q, J=7.2 Hz, 2H), 3.77 (s, 3H), 2.53 (s, 3H), 2.30 (s, 3H), 1.45 (t, J=7.2 Hz, 3H); ESI+ MS: m/z (rel intensity) 308.0 (100, M++H).

Provenance & Evidence