2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one → 3-(4-chloro-indazol-1-yl)-6-trifluoromethyl-1H-pyrimidine-2,4-dione

HRID 842542Notes

Reaction equation

HRID 842542 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[NH2:11].CN(C)[C:14]1[O:15][C:16](=[O:24])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[N:11]1[C:16](=[O:24])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[NH:19][C:14]1=[O:15]

Participants

4

Reactant 2

HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 226142584-Chloro-1H-indazol-1-amine

Product 1

HCID 226142623-(4-chloro-indazol-1-yl)-6-trifluoromethyl-1H-pyrimidine-2,4-dioneYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The crude 168A (1.15 g, 6.88 mmol assumed) is dissolved in glacial acetic acid (15 mL) and 2-dimethylamino4-trifluoromethyl-[1,3]oxazin-6-one (1.43 g, 6.88 mmol) is added. The mixture was stirred for 4 h under reflux, after which the acetic acid iss removed in vacuo. The residue is dissolved in ethyl acetate, washed with saturated sodium carbonate solution and water, and is subsequently dried over sodium sulfate. The crude product (1.9 g) is obtained after removal of the drying agent by filtration and evaporation of the solvent. The product (100 mg) is purified by flash chromatography (ethyl acetate/petrol ether 3/7).

Workup

  1. temperatureunder reflux
  2. customafter which the acetic acid iss removed in vacuo
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with saturated sodium carbonate solution and water
  5. dry with materialis subsequently dried over sodium sulfate

Sources & evidence

ORD record
ord-b6e945c33dfc4a66a0298cf46b2c015e
Source dataset
uspto-grants-2002_04
Patent number
US06376426B1

Reaction notes

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