3-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(benzyloxycarbonyl)methoxypyridine → 3-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-carboxymethoxypyridine

HRID 1862319Notes

Reaction equation

HRID 1862319 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([F:27])[C:24]([N:28]2[C:33](=[O:34])[CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[N:30]([CH3:39])[C:29]2=[O:40])=[CH:23][C:3]=1[O:4][C:5]1[C:6]([O:11][CH2:12][C:13]([O:15]CC2C=CC=CC=2)=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1>[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[CH:26]=[C:25]([F:27])[C:24]([N:28]2[C:33](=[O:34])[CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[N:30]([CH3:39])[C:29]2=[O:40])=[CH:23][C:3]=1[O:4][C:5]1[C:6]([O:11][CH2:12][C:13]([OH:15])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 186192133-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(benzyloxycarbonyl)methoxypyridine2×

Product 1

HCID 219335233-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-carboxymethoxypyridineYield 78.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.24 g of 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(benzyloxycarbonyl)methoxypyridine [present compound 7-82], 10 mg of 10% palladium/carbon and 1 ml of ethyl acetate was stirred for 1.5 hours at room temperature under hydrogen atmosphere. There action system was purged with nitrogen, then, the reaction solution was filtrated through Celite, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to obtain 0.16 g of 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-carboxymethoxypyridine [present compound 7-6].

Workup

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

Sources & evidence

ORD record
ord-266f8842f152498c9b77cf8fd1a8d0f7
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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