HCID 69718883, compound → HCID 21196302, compound

HRID 1066978Notes

Reaction equation

HRID 1066978 reaction equation
C([O:8][C:9]([CH2:11][N:12]1[CH:17]([C:18]2[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([F:26])[CH:19]=2)[C:16]([C:27]([O:29][CH3:30])=[O:28])=[C:15]([CH3:31])[N:14]=[C:13]1[CH3:32])=[O:10])C1C=CC=CC=1>CO.O.[Pd]>[CH3:30][O:29][C:27]([C:16]1[CH:17]([C:18]2[CH:19]=[C:20]([F:26])[C:21]([F:25])=[C:22]([F:24])[CH:23]=2)[N:12]([CH2:11][C:9]([OH:10])=[O:8])[C:13]([CH3:32])=[N:14][C:15]=1[CH3:31])=[O:28]

Participants

5

Reactant 1

HCID 69718883HCID 69718883, compound

Product 1

HCID 21196302HCID 21196302, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 10% Pd-C (30 mg) in MeOH (10 mL) and H2O (2 mL) was added a solution of 1,6-dihydro-1-{bezyloxycarbonylmethyl)-5-methoxycarbonyl-6-(3,4,5-trifluorophenyl)-2,4-dimethylpyrimidine (300 mg) in methanol (1 mL) and the mixture was hydrogenated at 80 psi for 4 h. The black suspension was filtered through a pad of Celite and washed thoroughly with MeOH (100 mL). Solvent was evaporated from the combined filtrate to leave the product 1,6-dihydro-5-methoxycarbonyl-6-(3,4,5-trifluorophenyl)-2,4-dimethylpyrimidine-1-acetic acid as a white solid (0.225 g). It was used in the next step without further purification.

Workup

  1. filtrationThe black suspension was filtered through a pad of Celite
  2. washwashed thoroughly with MeOH (100 mL)
  3. customSolvent was evaporated from the combined filtrate

Sources & evidence

ORD record
ord-a64317c6c04b431abe863ab5a736c143
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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