HCID 18619275, compound → HCID 178480549, compound

HRID 1862277Notes

Reaction equation

HRID 1862277 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[C:20]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])[C:19]([F:35])=[CH:18][C:17]=1[Cl:36])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:32])([F:31])[F:30])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:21][C:16]=1[O:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[OH:8]

Participants

4

Reactant 1

HCID 18619275HCID 18619275, compound

Product 1

HCID 178480549HCID 178480549, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.356 g of 4-benzyloxy-3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}pyridine, 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 0.32 g of 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-4-hydroxypyridine.

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-abd46d2ba2c04bc7ae59575ee42834b9
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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