Dimethyl Sulfoxide → 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask equipped with a magnetic stirrer was added 2,4-dichloropyrimidin-5-amine (1.89 g, 11.52 mmol), DIPEA (8.05 ml, 46.1 mmol), morpholine-3-carboxylic acid (1.66 g, 12.68 mmol), and DMSO (5 ml). The reaction was stirred at 100° C. overnight. The reaction mixture was poured into water and extracted with EtOAc 3 times. The pH of the aqueous layer was adjusted (about 5) with 10% citric acid and extracted again with EtOAc. The combined organic layer dried over MgSO4, filtered, and concentrated in vacuo to furnish a tan solid. The solid was triturated in diethyl ether containing a small amount of EtOH, filtered, and dried to give 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one: 1.95 g (70.3%). MS [M+H] found 241.

Provenance & Evidence