Water → HCID 18619240, compound

HRID 1862295Notes

Reaction equation

HRID 1862295 reaction equation
O.[F:2][C:3]1[C:23]([N:24]2[C:29](=[O:30])[CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]([CH3:35])[C:25]2=[O:36])=[CH:22][C:6]([O:7][C:8]2[C:9]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)=[C:5]([N+:37]([O-])=O)[CH:4]=1>C(O)(=O)C.[Fe]>[NH2:37][C:5]1[CH:4]=[C:3]([F:2])[C:23]([N:24]2[C:29](=[O:30])[CH:28]=[C:27]([C:31]([F:32])([F:34])[F:33])[N:26]([CH3:35])[C:25]2=[O:36])=[CH:22][C:6]=1[O:7][C:8]1[C:9]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 962WaterHCID 18619217HCID 18619217, compound

Product 1

HCID 18619240HCID 18619240, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
35 °C

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-4d9dd7d81f7343a3974a60fe06fd3598
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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