Dimethylformamide → 5-[3-(R)-fluoroheptyloxy]-2-(4-benzyloxyphenyl)pyrimidine

HRID 485993Notes

Reaction equation

HRID 485993 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.CS(O[CH2:27][CH2:28][C@H:29]([F:34])[CH2:30][CH2:31][CH2:32][CH3:33])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:34][C@H:29]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:28][CH2:27][O:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 227174625-Hydroxy-2-(4-benzyloxyphenyl)pyrimidineHCID 22850585HCID 22850585, compound

Product 1

HCID 228505975-[3-(R)-fluoroheptyloxy]-2-(4-benzyloxyphenyl)pyrimidineYield 88.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.12 g of 5-hydroxy-2-(4-benzyloxyphenyl)pyrimidine, 1.30 g of 3-(R)-fluoroheptyl methanesulfonate, 1.2 g of potassium carbonate, and 50 ml of DMF was stirred at 80° C. for 4 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and distilled to remove the solvent to obtain a residue weighing 2.12 g. Recrystallization of the residue from ethanol furnished 1.41 g (percent yield: 87.7%) of 5-[3-(R)-fluoroheptyloxy]-2-(4-benzyloxyphenyl)pyrimidine.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. distillationdistilled
  5. customto remove the solvent
  6. customto obtain a residue
  7. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-1e8f65eb38fd485ab0fa037232d5be83
Source dataset
uspto-grants-1994_03
Patent number
US05290477

Reaction notes

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