Tetrahydrofuran → 5-[2-(R)-Tetrahydropyranyloxyheptyloxy]-2-(4-hydroxyphenyl)pyrimidine

HRID 485996Notes

Reaction equation

HRID 485996 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:9][O:10][C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[CH:19][CH:18]=2)=[N:15][CH:16]=1.C1COCC1>CO>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:9][O:10][C:11]1[CH:16]=[N:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)=[N:13][CH:12]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 678491895-[2-(R)-Tetrahydropyranyloxyheptyloxy]-2-(4-benzyloxyphenyl)pyrimidine

Product 1

HCID 1363783735-[2-(R)-Tetrahydropyranyloxyheptyloxy]-2-(4-hydroxyphenyl)pyrimidineYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 2 l four-necked flask were charged 25.3 g (51.2 mmol) of the compound obtained in step 1, 506 ml of THF, and 506 ml of methanol. After purging the flask with nitrogen, 5 g of 10% palladium-on-carbon was added thereto to conduct hydrogenation at 30° to 35° C. under atmospheric pressure for 2 hours. After completion of the reaction, the catalyst was removed by filtration in a nitrogen stream, and the solvent was recovered to afford 20.18 g of the titled compound.

Workup

  1. customAfter purging the flask with nitrogen, 5 g of 10% palladium-on-carbon
  2. additionwas added
  3. customat 30° to 35° C.
  4. customfor 2 hours
  5. customAfter completion of the reaction
  6. customthe catalyst was removed by filtration in a nitrogen stream
  7. customthe solvent was recovered

Sources & evidence

ORD record
ord-fa10367fb9ea48889784bf893b3a423e
Source dataset
uspto-grants-1994_03
Patent number
US05290477

Reaction notes

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