HCID 57072329, compound → 4-Pyrimidineethanol, α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-, 4-(dihydrogen phosphate), (αR,βS)-

HRID 1006650Notes

Reaction equation

HRID 1006650 reaction equation
[P:1]([O:19][C@@:20]([C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[F:43])([C@H:27]([C:29]1[C:34]([F:35])=[CH:33][N:32]=[CH:31][N:30]=1)[CH3:28])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2]>CO.[OH-].[OH-].[Pd+2]>[P:1]([OH:11])([OH:3])([O:19][C@@:20]([C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[F:43])([C@H:27]([C:29]1[C:34]([F:35])=[CH:33][N:32]=[CH:31][N:30]=1)[CH3:28])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)=[O:2]

Participants

4

Reactant 1

HCID 57072329HCID 57072329, compound

Product 1

HCID 235198664-Pyrimidineethanol, α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-, 4-(dihydrogen phosphate), (αR,βS)-Yield 49%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of the compound of step (a) (5.0 g, 8.83 mmol) in methanol (100 ml) was hydrogenated over Pearlman's catalyst (1.0 g) at room temperature and at 414 kPa (60 p.s.i.) for 16 hours. The solution was filtered through a pad of celite (trade mark) and concentrated. The crude product was redissolved in hot methanol (20 ml) and granulated at 0° C. for 1 hour. After filtering and washing with methanol (5 ml) the product was dried under vacuum at 50° C. to give the title compound (1.72 g, 49%). m.p. 145-146° C.

Workup

  1. filtrationThe solution was filtered through a pad of celite (trade mark)
  2. concentrationconcentrated
  3. dissolutionThe crude product was redissolved in hot methanol (20 ml)
  4. filtrationAfter filtering
  5. washwashing with methanol (5 ml) the product
  6. customwas dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-bef97d2c56a5407b81af7c947e080cd7
Source dataset
uspto-grants-2004_09
Patent number
US06790957B2

Reaction notes

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