Water → HCID 18619271, compound

HRID 1862242Notes

Reaction equation

HRID 1862242 reaction equation
O.[Cl:2][C:3]1[CH:18]=[C:17]([F:19])[C:16]([N:20]2[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]([CH3:31])[C:21]2=[O:32])=[CH:15][C:4]=1[O:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][N:7]=1>C(O)(=O)C.[Fe]>[NH2:12][C:11]1[C:6]([O:5][C:4]2[CH:15]=[C:16]([N:20]3[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]([CH3:31])[C:21]3=[O:32])[C:17]([F:19])=[CH:18][C:3]=2[Cl:2])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 962WaterHCID 18619192HCID 18619192, compound

Product 1

HCID 18619271HCID 18619271, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
35 °C

Procedure

To a mixture of 3.8 g of an iron powder, 50 ml of acetic acid and 5 ml of water was added a solution of 3.8 g of 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-3-nitropyridine in 5.0 ml of acetic acid dropwise while maintaining the temperature of the reaction solution at 35° C. or lower. After completion of the addition, the mixture was stirred for 2 hours, then, the reaction solution was filtrated through Celite, and diluted with ethyl acetate. The mixture was neutralized with saturated aqueous sodium bicarbonate solution, the organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated, then, the resulted residue was subjected to silica gel chromatography to obtain 3.4 g of 3-amino-2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}pyridine.

Workup

  1. additionAfter completion of the addition
  2. filtrationthe reaction solution was filtrated through Celite
  3. additiondiluted with ethyl acetate
  4. washthe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b65a794190a74bd997c8515da0beca37
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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