Phosphorus oxychloride → methyl 2-amino-4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate

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Reaction Conditions

Reaction Steps

Phosphorus oxychloride (16.0 mL, 172 mmol) was added to methyl 2-amino-4-hydroxy-6,7-dihydro-5H-cyclopenta[d]pyrimidine-5-carboxylate (5.84 g, 27.9 mmol). The resulting mixture was heated in a sealed tube at 100° C. in the microwave for 3 hours. The solvent was evaporated. The residue was dissolved in 6 mL acetonitrile and 6 mL ice/water was added. The resulting mixture was stirred at RT for 15 minutes and purified by reverse phase preparative HPLC on a SunFire column using a gradient from 0 to 100% acetonitrile over 10 minutes (11 injections) to afford the title compound. Additional product was obtained by re-purification of mixed fractions: LC/MS (M+H)=228, 230.

Provenance & Evidence