Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2386229Generated: October 31, 2026

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

https://huagongshe.com/reaction/2386229

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
ReactantDiisopropylethylamineHCID 81531—
ReactantMorpholine-3-carboxylic acid hydrochlorideHCID 45790954—
Reactant2,4-dichloro-N-isopropylpyrimidin-5-amineHCID 86651569—
SolventWaterHCID 962—
Product2-chloro-5-isopropyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-oneHCID 8665157093.1%

Reaction Conditions

Temperature100 °C

Reaction Steps

A round-bottom flask was charged with 2,4-dichloro-N-isopropylpyrimidin-5-amine (940 mg, 4.56 mmol), morpholine-3-carboxylic acid hydrochloride (994 mg, 5.93 mmol), DIPEA (3.19 mL, 18.25 mmol) and DMSO (8 mL). The flask was heated overnight at 100° C. The solution was diluted with water and refrigerated for 2 hours. The aqueous solution was extracted twice with EtOAc. The organic layers were combined, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 2-chloro-5-isopropyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one as a brown solid (1.2 g). MS [M+H] Found 283.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08268819B2
Source datasetuspto-grants-2012_09
ORD IDord-99b8d1d8cdd04fad851f79152d1530d5
Source noteuspto-grants-2012_09