Water → HCID 18619252, compound

HRID 1862307Notes

Reaction equation

HRID 1862307 reaction equation
O.[F:2][C:3]1[C:21]([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:20][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:12][CH:13]=2)=[C:5]([N+:35]([O-])=O)[CH:4]=1>C(O)(=O)C.[Fe]>[NH2:35][C:5]1[CH:4]=[C:3]([F:2])[C:21]([N:22]2[C:27](=[O:28])[CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[N:24]([CH3:33])[C:23]2=[O:34])=[CH:20][C:6]=1[O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N:12][CH:13]=1

Participants

5

Reactant 2

HCID 962WaterHCID 18619205HCID 18619205, compound

Product 1

HCID 18619252HCID 18619252, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
35 °C

Procedure

To a mixed solution of 1.2 g of an iron powder, 5 ml of acetic acid and 0.5 ml of water was added a solution of 0.93 g of 5-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]-2-nitrophenoxy}-2-(methoxycarbonyl)methoxypyridine in 4 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, filtrated through Celite, and concentrated. The residue was diluted with water, and extracted with ethyl acetate. The organic layer was mixture was washed with saturated aqueous sodium bicarbonate solution, then saturated saline, dried over anhydrous magnesium sulfate, and concentrated. Then, the resulted residue was subjected to silica gel chromatography to obtain 0.83 g of 5-{2-amino-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine.

Workup

  1. additionAfter completion of the addition
  2. filtrationfiltrated through Celite
  3. concentrationconcentrated
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washwas washed with saturated aqueous sodium bicarbonate solution
  7. dry with materialsaturated saline, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1da4046787f44d6e88b2b4c275dc1eee
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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