Water → 3-Amino-6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxypyridine

HRID 1862326Notes

Reaction equation

HRID 1862326 reaction equation
O.[Cl:2][C:3]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:4]=1[O:5][C:6]1[N:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([N+:20]([O-])=O)=[CH:8][CH:7]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:20][C:9]1[C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:11][C:6]([O:5][C:4]2[CH:23]=[C:24]([N:28]3[C:33](=[O:34])[CH:32]=[C:31]([C:35]([F:38])([F:36])[F:37])[N:30]([CH3:39])[C:29]3=[O:40])[C:25]([F:27])=[CH:26][C:3]=2[Cl:2])=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 962WaterHCID 186191896-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxy-3-nitropyridine

Product 1

HCID 186191973-Amino-6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxypyridineYield 89.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

To a mixed solution of 3.0 g of an iron powder, 15 ml of acetic acid and 1.5 ml of water was added a solution of 3.0 g of 6-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxy-3-nitropyridine in 10 ml of acetic acid and 10 ml of ethyl acetate dropwise while maintaining the temperature of the reaction solution at 35° C. or lower. After completion of the addition, the mixture was stirred over night, then, the reaction solution was filtrated through Celite, and the solvent was removed at reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate solution, extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The resulted residue was subjected to silica gel chromatography to obtain 2.55 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-benzyloxypyridine

Workup

  1. additionAfter completion of the addition
  2. filtrationthe reaction solution was filtrated through Celite
  3. customthe solvent was removed at reduced pressure
  4. additionThe residue was diluted with saturated aqueous sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4cdc7046e771452da8b3cb55bc9afa4b
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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