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

HRID 2386229Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1.Cl.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH:15]1[C:20](O)=[O:21].CCN(C(C)C)C(C)C.CS(C)=O>O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:9]([CH:10]([CH3:12])[CH3:11])[C:20](=[O:21])[CH:15]3[CH2:16][O:17][CH2:18][CH2:19][N:14]3[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

extractionThe aqueous solution was extracted twice with EtOAc
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-99b8d1d8cdd04fad851f79152d1530d5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268819B2

Reaction notes

Loading…