Water → HCID 13608179, compound

HRID 1905872Notes

Reaction equation

HRID 1905872 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]([CH2:15][CH3:16])[C:13](=[O:17])[N:12]([CH3:18])[C:11](=[N:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[F-].[K+].Br[CH2:32][CH2:33]Br.O>CN(C)C=O>[CH2:32]1[CH2:33][O:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]3[N:14]([CH2:15][CH3:16])[C:13](=[O:17])[N:12]([CH3:18])[C:11](=[N:19][C:20]4[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=4[CH3:28])[CH:10]=3)=[CH:3][C:2]=2[O:1]1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 522689Potassium FluorideHCID 135782138HCID 135782138, compound

Product 1

HCID 13608179HCID 13608179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3,4-dihydro-6-(3,4-dihydroxyphenyl)--ethyl-3-methyl-4-(2,4,6-trimethylphenylimino)-2(1H)pyrimidinone (1.0 g) in dimethylformamide (30 ml) were added spray-dried potassium fluoride (0.77 g) and 1,2-dibromoethane (0.25 ml). The mixture was stirred at 110° C. for 2.5 hours. The reaction mixture was poured into water and extracted with diethyl ether. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica gel and eluted with chloroform. The fractions containing the desired compound were combined and concentrated under reduced pressure to give 3,4-dihydro-6-(3,4-ethylenedioxyphenyl)-1-ethyl-3-methyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (0.3 g).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. washeluted with chloroform
  6. additionThe fractions containing the desired compound
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1e345d916644fe3b758b4c162f4ccbc
Source dataset
uspto-grants-1987_03
Patent number
US04649142

Reaction notes

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