Water → HCID 135782139, compound

HRID 1905880Notes

Reaction equation

HRID 1905880 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]([CH3:15])[C:13](=[O:16])[N:12]([CH3:17])[C:11](=[N:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[H-].[Na+].[CH3:30]I.O>CN(C)C=O>[CH3:15][N:14]1[C:9]([C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([O:1][CH3:30])[CH:3]=2)=[CH:10][C:11](=[N:18][C:19]2[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=2[CH3:27])[N:12]([CH3:17])[C:13]1=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1357821373,4-dihydro-6-(3,4-dihydroxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone

Product 1

HCID 135782139HCID 135782139, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dihydro-6-(3,4-dihydroxyphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)pyrimidinone (2.0 g) in N,N-dimethylformamide (20 ml) were added sodium hydride (60% in Nujol, 0.22 g) and methyl iodide (0.37 ml), and the mixture was stirred at ambient temperature for 2 hours. Then the reaction mixture was poured into water (200 ml), and extracted with ethyl acetate. The organic extract was washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel eluting with chloroform to give 3,4-dihydro-1,3-dimethyl-6-(4-hydroxy-3-methoxyphenyl)-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (0.66 g).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-7bc6dc991d1a445ca76b4c713e203782
Source dataset
uspto-grants-1987_03
Patent number
US04649142

Reaction notes

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