HCID 18619178, compound → HCID 18619231, compound

HRID 1862345Notes

Reaction equation

HRID 1862345 reaction equation
C([O:8][C:9]1[C:10]([O:15][C:16]2[CH:21]=[C:20]([N:22]3[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]3=[O:34])[C:19]([F:35])=[CH:18][C:17]=2[Cl:36])=[N:11][CH:12]=[N:13][CH:14]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[Cl:36][C:17]1[CH:18]=[C:19]([F:35])[C:20]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:21][C:16]=1[O:15][C:10]1[C:9]([OH:8])=[CH:14][N:13]=[CH:12][N:11]=1

Participants

4

Reactant 1

HCID 18619178HCID 18619178, compound

Product 1

HCID 18619231HCID 18619231, compoundYield 103.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.959 g of 5-benzyloxy-4-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}pyrimidine, 10% palladium/carbon and ethyl acetate was stirred for 8 hours at room temperature under hydrogen atmosphere. The reaction system was purged with nitrogen, then, the reaction solution was filtrated through Celite, and the filtrate was concentrated to obtain 0.824 g of 4-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-5-hydroxypyrimidine.

Workup

  1. customThe reaction system was purged with nitrogen
  2. filtrationthe reaction solution was filtrated through Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b7f41a503c9c42ee8ed9c4d8c26bae54
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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