Potassium Carbonate → 5-[2-(R)-Tetrahydropyranyloxyheptyloxy]-2-(4-benzyloxyphenyl)pyrimidine

HRID 485995Notes

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.S(C1C=CC(C)=CC=1)(O[CH2:26][C@H:27]([O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH:34]1[O:33][C@H:27]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:26][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

Conditions

Temperature: 80 °C

Procedure

In a 500 ml four-necked flask were charged 12.2 g (43.7 mmol) of 5-hydroxy-2-(4-benzyloxyphenyl)pyrimidine, 24 g (65.5 mmol) of (R)-2-tetrahydropyranyloxyheptyl tosylate, 12 g of potassium carbonate, and 183 ml of DMF, and the mixture was stirred at 80° C. for 5 hours. After cooling, the reaction mixture was poured into 500 ml of ice-water and extracted with ethyl acetate. The extract was washed with water, and the solvent was removed by distillation under reduced pressure to obtain 28.6 g of a crude product, which was purified by silica gel column chromatography to obtain 25.3 g of the titled compound.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washThe extract was washed with water
customthe solvent was removed by distillation under reduced pressure
customto obtain 28.6 g of a crude product, which
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-67e3832e51cf4097a650e3c83aadf71a
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290477

Reaction notes

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