Sodium hydride → HCID 77107830, compound

Participants

Reaction Steps

Sodium hydride (60% wt in mineral oil, 6.69 mg, 0.167 mmol) was added to a solution of 2-chloroethyl((10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-2,4-dioxo-2,3,4,7,8,10-hexahydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazin-8-yl)methyl)carbamate (48.9 mg, 0.084 mmol) in THF (4 mL). The mixture was heated at reflux for 18 hours. A further portion of sodium hydride (60% wt in mineral oil, 33.4 mg, 0.836 mmol) was added and the mixture heated at reflux for a further 2 days. The mixture was cooled to room temperature, quenched with water (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic extracts were washed with brine, passed through a hydrophobic frit and evaporated under vacuum. Purification by mass-directed HPLC under the following conditions afforded the title compound as a mixture of diastereomers.

Provenance & Evidence