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

HRID 1726361Notes

Reaction equation

HRID 1726361 reaction equation
[Na].[CH3:2][C:3]1[O:4][C:5](=O)[C:6](=[CH:8][OH:9])[N:7]=1.Cl.[CH3:12][O:13][C:14](=[NH:16])[NH2:15]>C(#N)C>[CH3:12][O:13][C:14]1[NH:16][C:8](=[O:9])[C:6]([NH:7][C:3](=[O:4])[CH3:2])=[CH:5][N:15]=1

Participants

4

Reactant 2

HCID 3083899Carbamimidic acid, methyl ester, hydrochloride (1:1)HCID 178432983HCID 178432983, compound

Product 1

HCID 116583982-Methoxy-6-oxo-5-acetylamino-1,6-dihydropyrimidineYield 74.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Acetonitrile (20 ml) was added to 2-methyl-4-hydroxymethylene-5-oxazolone sodium salt (1.00 g, 6.71 mmol) and O-methylisourea hydrochloride (0.74 g, 6.71 mmol), and the mixture was stirred at 80° C. for 2 days. The mixture was concentrated, and methanol (5 ml) and water (3 ml) were added. 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-acetylamino-1,6-dihydropyrimidine (0.91 g, 4.97 mmol).

Workup

  1. concentrationThe mixture was concentrated
  2. additionmethanol (5 ml) and water (3 ml) were added
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. filtrationThen, the precipitate was collected by filtration and vacuum
  5. customdried

Sources & evidence

ORD record
ord-5edab0e60d0e4915acbf614d6cb7528b
Source dataset
uspto-grants-2009_02
Patent number
US07491822B2

Reaction notes

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