Carbamimidic acid, methyl ester, hydrochloride (1:1) → 2-Methoxy-6-oxo-5-phenylacetylamino-1,6-dihydropyrimidine

HRID 1726360Notes

Reaction equation

[Na].[CH2:2]([C:9]1[O:10][C:11](=O)[C:12](=[CH:14][OH:15])[N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[CH3:18][O:19][C:20](=[NH:22])[NH2:21]>C(#N)C>[CH3:18][O:19][C:20]1[NH:22][C:14](=[O:15])[C:12]([NH:13][C:9](=[O:10])[CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:11][N:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Acetonitrile (15 ml) was added to 2-benzyl-4-hydroxymethylene-5-oxazolone sodium salt (1.00 g, 4.44 mmol) and O-methylisourea hydrochloride (0.49 g, 4.44 mmol), and the mixture was stirred overnight at 80° C. The mixture was concentrated under reduced pressure, water (5 ml) was added, and the mixture was stirred at room temperature for 1 hour. Then, the precipitate was collected by filtration and vacuum dried to give 2-methoxy-6-oxo-5-phenylacetylamino-1,6-dihydropyrimidine (0.94 g, 3.64 mmol).

Workup

concentrationThe mixture was concentrated under reduced pressure, water (5 ml)
additionwas added
stirringthe mixture was stirred at room temperature for 1 hour
filtrationThen, the precipitate was collected by filtration and vacuum
customdried

Sources & evidence

ORD record: ord-fdffd7be3df54efeb2a8c39a896357f3
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491822B2

Reaction notes

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