5-Acetyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine → 6-Methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylic acid

HRID 255732

Reaction equation

HRID 255732 reaction equation
[C:1]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[N:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:9]=1[CH3:10])(=[O:3])C.Br[O-].[Na+].S(=O)(O)[O-:30].[Na+]>O1CCCC1>[CH3:10][C:9]1[N:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:4]=1[C:1]([OH:30])=[O:3]

Participants

5

Reactant 3

HCID 151474775-Acetyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidineHCID 23665763Sodium BisulfiteHCID 23673712Sodium hypobromite

Product 1

HCID 151474876-Methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-acetyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.5 g), tetrahydrofuran (70 ml), sodium hypobromite (70 ml) was stirred for 2 hours at ambient temperature. To the mixture was added an aqueous sodium bisulfite solution. The mixture was washed with diethyl ether (100 ml) and the aqueous solution was acidified to pH 3.0 with 10% hydrochloric acid. The resultant crystals were collected by filtration to give 0.80 g of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylic acid.

Workup

  1. washThe mixture was washed with diethyl ether (100 ml)
  2. filtrationThe resultant crystals were collected by filtration

Sources & evidence

ORD record
ord-19c85a267351462d806f23799a5721f5
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Linked notes

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