Diisopropylamine → HCID 67200186, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6 M in hexanes, 67 ml, 107 mmol) is added dropwise to a stirred solution of diisopropylamine (15 ml, 107 mmol) in dry THF (90 ml) under argon at −78° C. After 15 minutes at −78° C. to 50° C. the mixture is cooled to −78° C. and a solution of 4,6-dimethyl-2-methylsulfanyl-pyrimidine (15 g, 97.4 mmol) in dry THF (45 ml) is added dropwise. The reaction is stirred for 2.5 hours at −78° C. then N-methoxy-N-methylacetamide (10.4 ml, 97.4 mmol) is added dropwise. The reaction is allowed to warm to room temperature over 1 hour followed by quenching with saturated aqueous ammonium chloride solution (10 ml). The mixture is concentrated to remove most of the THF then partitioned between water (200 ml) and DCM (200 ml). The organic extract is separated, dried (MgSO4), and the solvent is removed to afford the titled compound. The material is a mixture of keto and enol forms as observed by 1H nmr (CDCl3)

Provenance & Evidence