p-Toluenesulfonic acid → 5-(2,3-Difluoro-4-hydroxyphenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidine

HRID 376764Notes

Reaction equation

HRID 376764 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[N:28][C:29]([C:32]3[CH:33]=[N:34][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:36][CH:37]=3)=[N:30][CH:31]=2)=[C:22]([F:45])[C:21]=1[F:46])C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[F:45][C:22]1[C:21]([F:46])=[C:20]([OH:19])[CH:25]=[CH:24][C:23]=1[C:26]1[CH:31]=[N:30][C:29]([C:32]2[CH:33]=[N:34][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:36][CH:37]=2)=[N:28][CH:27]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 178693985-(4-Benzyloxy-2,3-difluorophenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 193591085-(2,3-Difluoro-4-hydroxyphenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidineYield 74.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of 10 percent palladium/charcoal and 0.1 g of 4-toluenesulfonic acid are added to a solution of 14 mmol of 5-(4-benzyloxy-2,3-difluorophenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidine in 200 ml of THF. The mixture is stirred at 50° C. under hydrogen in a suitable apparatus until the take-up of hydrogen is complete, the catalyst is filtered off, and the solvent is removed in vacuo. Purification by recrystallization from acetonitrile gives 4.0 g (73%) of a colorless solid, m.p. 150-155° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. customPurification
  4. customby recrystallization from acetonitrile

Sources & evidence

ORD record
ord-560ae4ef0e544c738813490c03d4ef52
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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