Ethyl 2-methylacetoacetate → HCID 178432490, compound

Participants

Reaction Steps

A solution of sodium ethoxide (previously prepared by dissolving sodium (6.36 g, 278 mmol, 3 eq) in EtOH (300 ml)), stirring at RT, was treated with ethyl 2-methyl-3-oxobutanoate (16.94 ml, 120 mmol, 1.3 eq). A slurry of cyclohexanecarboximidamide hydrochloride (15 g, 92 mmol, 1 eq) in EtOH (100 ml) was then added and the RM heated at reflux for 8 h. The RM was concentrated, water added and the pH adjusted to ˜7-8 with 2N HCl. Following acidification a white solid precipitated and this was filtered and dried in the vac-oven to yield 2-cyclohexyl-5,6-dimethylpyrimidin-4-ol as a white solid (28.91 g, 151%). 1H (400 MHz, DMSO) 1.03-1.86 (10H, m), 1.96 (3H, s), 2.16 (3H, s), 2.36-2.57 (1H, m), 12.05 (1H, brs); ES+207.

Provenance & Evidence