Guanidine Hydrochloride → Methyl 2-amino-6,7-dihydro-5H-cyclopenta[d]pyrimidine-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-[(dimethylamino)methylidene]-4-oxocyclopentanecarboxylate (71.7 mg, 0.36 mmol) in anhydrous methanol (2.5 mL) was added guanidine hydrochloride (124.7 mg, 1.3 mmol) followed by sodium methoxide in methanol (0.24 mL, 1.27 mmol). The mixture was heated to 90° C. in a sealed tube overnight. The crude reaction was quenched with 2 N HCl and concentrated in vacuo. The aqueous residue was purified by HPLC (30×100 mm Waters Sunfire column; 5 micron; 35 mL/min.; 210 nM; 0% to 40% CH3CN+0.05% TFA/water+0.05% TFA over 15 min.; the compound eluted at 10% CH3CN+0.05% TFA/water+0.05% TFA) to afford the title compound after lyophilization.

Provenance & Evidence