HCID 22725146, compound → HCID 22725208, compound

HRID 1066971Notes

Reaction equation

HRID 1066971 reaction equation
C([O:8][C:9]([C:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=2)[N:15]([C:25]([O:27][CH3:28])=[O:26])[C:14]([O:29]C)=[N:13][C:12]=1[CH2:31][CH3:32])=[O:10])C1C=CC=CC=1>CO.[Pd]>[CH2:31]([C:12]1[NH:13][C:14](=[O:29])[N:15]([C:25]([O:27][CH3:28])=[O:26])[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=2)[C:11]=1[C:9]([OH:10])=[O:8])[CH3:32]

Participants

4

Reactant 1

HCID 22725146HCID 22725146, compound

Product 1

HCID 22725208HCID 22725208, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (−)-5-(benzyloxycarbonyl)-4-ethyl-1,6-dihydro-2-methoxy-6-(3,4-difluorophenyl)-1-[methoxycarbonyl]pyrimidine (0.45 g, 1.18 mmol) in 20 mL of MeOH was added 0.05 g of 10% Pd on carbon and the resulting suspension was hydrogenated under 100 psi for 12 h. The catalyst was then filtered through a pad of celite and was washed thoroughly with MeOH. All the MeOH washings were collected and the solvent was removed in vacuo to obtain 0.42 g (99% yield) of (−)-1,2,3,6-tetrahydro-4-ethyl-2-oxo-6-(3,4-difluorophenyl)-1-[methoxycarbonyl]pyrimidine-5-carboxylic acid as a white solid which was used in the next reaction without further purification.

Workup

  1. filtrationThe catalyst was then filtered through a pad of celite
  2. washwas washed thoroughly with MeOH
  3. customAll the MeOH washings were collected
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-690d60bb2a1b422ba64155e6b4dbc91f
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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