Acetonitrile → 2-Methoxy-6-oxo-5-phenylacetylamino-1,6-dihydropyrimidine

HRID 1726362Notes

Reaction equation

HRID 1726362 reaction equation
Cl.[CH3:2][O:3][C:4](=[NH:6])[NH2:5].C[O-].[Na+].C(#N)C.[CH2:13]([C:20]1[O:21][C:22](=[O:27])[C:23](=[CH:25]O)[N:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO.O>[CH3:2][O:3][C:4]1[NH:5][C:22](=[O:27])[C:23]([NH:24][C:20](=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:25][N:6]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 3083899Carbamimidic acid, methyl ester, hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 178519093HCID 178519093, compound

Product 1

HCID 114595982-Methoxy-6-oxo-5-phenylacetylamino-1,6-dihydropyrimidineYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

O-Methylisourea hydrochloride (0.11 g, 1.0 mmol) was dissolved in methanol (2 ml), and 28% sodium methoxide (0.19 g, 1.0 mmol) was added. Acetonitrile was added, and the mixture was concentrated. 2-Benzyl-4-hydroxymethylene-5-oxazolone (0.203 g, 1.00 mmol) was added, and the mixture was stirred overnight at 80° C. Water (3 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 (0.16 g, 0.62 mmol). The values of the shift in 1H-NMR were the same as those in Example 1.

Workup

  1. concentrationthe mixture was concentrated
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationThen, the precipitate was collected by filtration and vacuum
  4. customdried

Sources & evidence

ORD record
ord-1fa938b1f9444bde86dca1816bd1dd25
Source dataset
uspto-grants-2009_02
Patent number
US07491822B2

Reaction notes

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