Water → HCID 86651595, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,4-dichloro-N-(tetrahydro-2H-thiopyran-4-yl)pyrimidin-5-amine (864 mg, 3.27 mmol) and morpholine-3-carboxylic acid hydrochloride (822 mg, 4.91 mmol) in DMSO (15 ml) was added diisopropylethylamine (2.29 ml, 13.1 mmol), and the reaction mixture was stirred at 95° C. for 4 hours. The reaction mixture was poured into water and extracted with EtOAc. The organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. The solid was chromatographed by silica gel (hexane/ethyl acetate, 19:1 to 3:2) to afford partially purified 2-chloro-5-(tetrahydro-2H-thiopyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (83.6 mg, 0.245 mmol, 7.5% yield) as a white solid. MS [M+H] found 341.

Provenance & Evidence