Potassium Carbonate → 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

HRID 1862325Notes

Reaction equation

HRID 1862325 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[N:29]([CH3:38])[C:28]2=[O:39])=[CH:22][C:21]=1[OH:40].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:35])([F:37])[F:36])[N:29]([CH3:38])[C:28]2=[O:39])=[CH:22][C:21]=1[O:40][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 225652672-(Benzyloxy)-6-chloro-3-nitropyridine

Product 1

HCID 186191896-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-benzyloxy-3-nitropyridineYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.29 g of 6-chloro-2-benzyloxy-3-nitropyridine, 6.77 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenol, 3.32 g of potassium carbonate and 30 ml of N,N-dimethylformamide was stirred for 30 minutes at room temperature, then at 50° C. for 2.5 hours. The resulted residue was added to ice water, extracted with ethyl acetate, and organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was recrystallized from ethyl acetate and hexane to obtain 9.11 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.

Workup

  1. waitat 50° C. for 2.5 hours
  2. extractionextracted with ethyl acetate, and organic layer
  3. washwas washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-aec1f7136a2249ccabf08ca313067b73
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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