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Dimethylformamide → 5-Methoxy-2-(4-benzyloxyphenyl)pyrimidine

HRID 485991
Notes
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Reaction equation

HRID 485991 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)=[N:5][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1357369415-Methoxy-2-(4-hydroxyphenyl)pyrimidine

Product 1

HCID 190970605-Methoxy-2-(4-benzyloxyphenyl)pyrimidineYield 64.7%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of 9.0 g of 5-methoxy-2-(4-hydroxyphenyl)pyrimidine, 8.45 g of benzyl chloride, 270 ml of dimethylformamide (DMF), and 12.3 g of potassium carbonate was stirred at 80° C. for 4 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and distilled to remove ethyl acetate to obtain 8.42 g (percent yield: 64.2%) of 5-methoxy-2-(4-benzyloxyphenyl)pyrimidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. distillationdistilled
  4. customto remove ethyl acetate

Sources & evidence

ORD record
ord-d6fcca4f37c54d1d96d3954441d8c3e1
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05290477

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes