Sodium Hydroxide → 3,4-dihydro-6-(3,4-dihydroxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone

HRID 1905879Notes

Reaction equation

HRID 1905879 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH3:17])[C:15](=[O:18])[N:14]([CH3:19])[C:13](=[N:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.[OH-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH3:17])[C:15](=[O:18])[N:14]([CH3:19])[C:13](=[N:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 98435333,4-dihydro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone

Product 1

HCID 1357821373,4-dihydro-6-(3,4-dihydroxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinoneYield 95%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)pyrimidinone (5.0 g) in aqueous hydrobromic acid (47%) (50 ml) was refluxed for 1.5 hours. After being cooled to ambient temperature, the solution was neutralized with aqueous sodium hydroxide, and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The resulting oil was crystallized from a mixture of diisopropyl ether and ethyl acetate (1:1 v/v) to give 3,4-dihydro-6-(3,4-dihydroxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (4.41 g).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe resulting oil was crystallized from a mixture of diisopropyl ether and ethyl acetate (1:1 v/v)

Sources & evidence

ORD record
ord-ed70c93cc5034cd09832164b650f27e9
Source dataset
uspto-grants-1987_03
Patent number
US04649142

Reaction notes

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