HCID 18619280, compound → HCID 18619232, compound

HRID 1862281Notes

Reaction equation

HRID 1862281 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([F:24])[C:21]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]2=[O:37])=[CH:20][C:3]=1[O:4][C:5]1[N:10]=[C:9]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:8]([N+:17]([O-])=O)=[CH:7][CH:6]=1>[Pd].C(OCC)(=O)C>[NH2:17][C:8]1[C:9]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:10][C:5]([O:4][C:3]2[CH:20]=[C:21]([N:25]3[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[N:27]([CH3:36])[C:26]3=[O:37])[C:22]([F:24])=[CH:23][C:2]=2[Cl:1])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 18619280HCID 18619280, compound

Product 1

HCID 18619232HCID 18619232, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.25 g of 6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxy-3-nitropyridine, 0.3 g of 10% palladium/carbon and 40 ml of ethyl acetate was stirred for 3 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. The residue was subjected to silica gel column chromatography to obtain 1.38 g of 3-amino-6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine.

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-30332139b67f4183af4490a9deaa740c
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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