2-Methyl-2-butene → HCID 11196946, compound

HRID 650251Notes

Reaction equation

HRID 650251 reaction equation
CC(=CC)C.P([O-])(O)(O)=O.[Na+].Cl([O-])=[O:13].[Na+].[C:16]([NH:19][C:20]1[C:25](=[O:26])[N:24]([CH2:27][CH:28]=[O:29])[C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:22][CH:21]=1)(=[O:18])[CH3:17]>>[C:16]([NH:19][C:20]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([OH:13])=[O:29])[C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:22][CH:21]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 54308999HCID 54308999, compound

Product 1

HCID 11196946HCID 11196946, compound

Procedure

2-Methyl-2-butene (1.38 ml, 12.98 mmol), an aqueous solution (4.2 ml) of sodium dihydrogen phosphate.1H2O (419 mg, 2.95 mmol) and an aqueous solution (9.3 ml) of sodium chlorite (934 mg, 10.32 mmol) were added to a solution of (5-acetylamino-6-oxo-2-phenyl-1,6-dihydropyrimidine-1-yl)acetaldehyde(800mg,2.95 mmol) in2-methyl-2-propanol (14.8 ml), and the mixture was stirred overnight at room temperature. The reaction solution was washed with diethyl ether, and then the aqueous layer was adjusted to pH, 4 with citric acid and extracted 6 times with methylene chloride. After dried over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure whereby 5-acetylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidyl acetic acid (537 mg, 63%) was obtained as white solid.

Workup

  1. washThe reaction solution was washed with diethyl ether
  2. extraction4 with citric acid and extracted 6 times with methylene chloride
  3. dry with materialAfter dried over anhydrous sodium sulfate
  4. concentrationthe organic layer was concentrated under reduced pressure whereby 5-acetylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidyl acetic acid (537 mg, 63%)
  5. customwas obtained as white solid

Sources & evidence

ORD record
ord-637e4b57b3ba4e228fb1c7517037bd5c
Source dataset
uspto-grants-2001_08
Patent number
US06271238B1

Reaction notes

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