Methanol → HCID 58826024, compound

Participants

Reaction Steps

To a solution of 5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (1.0 g, 2.5 mmoles) in CH2Cl2 (80 ml) cooled at 0° C. was added pyridine (2.6 g, 36 mmole) and trimethylsilylchloride (2.70 g, 25 mmole). The reaction mixture was stirred at room temperature for two hours, then recooled to 0° C. and acetyl chloride (0.22 g, 2.75 mmole) was added dropwise. After stirring at 0° C. for 90 minutes, methanol (20 ml) was added and stirring was continued for 16 hours. Solvent was removed under reduced pressure and the residue was treated with water (400 ml). The white insoluble material was collected by filtration and subject to flash chromatography on silica gel, eluting with 2% CH3OH, 0.1% NH4OH in CH2Cl2 to give N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-acetamide (0.094 g, MS (M+H)=443), N-[2-Acetylamino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-4-yl]-acetamide (0.187 g, MS (M+H)=485), and a third fraction containing a mixture of N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-acetamide and N-[2-Acetylamino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-4-yl]-acetamide (0.524 g).

Provenance & Evidence