Methanol → 6-tert-Butyl 3-methyl (S)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-3,6-dicarboxylate

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Reaction Steps

To a solution of dimethyl methoxymethylene malonate (8.68 g, 49.8 mmol) in 100 mL MeOH at −10° C., was added a solution of 1e (8.50 g, 46.1 mmol) in 100 mL MeOH over 1 h. The mixture was stirred at rt for 2 h, then was allowed to warm to rt overnight. The mixture was concentrated in vacuo and the resultant residue was purified by flash chromatography (50 to 100% EtOAc/hexanes) to afford 6.32 g (46%) of pyrimidinone 1f, as a colorless solid. 1H NMR (300 MHz, CDCl3) δ8.69 (s, 1H), 5.03 (dd, J=9.7, 2.8, 1H), 3.90 (s, 3H), 3.38-3.09 (m, 2H), 2.64-2.49 (m, 1H), 2.34-2.23 (m, 1H), 1.49 (s, 9H).

Provenance & Evidence