Picolyl chloride hydrochloride → HCID 19912195, compound

HRID 1090969Notes

Reaction equation

HRID 1090969 reaction equation
[F:1][C:2]1[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[H-].[Na+].Cl.Cl[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1>CN(C)C=O>[F:1][C:2]1[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:11][C:5]2[N:6]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 15544298HCID 15544298, compound

Product 1

HCID 19912195HCID 19912195, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.20 g of 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione was added at room temperature to an N,N -dimethylformamide solution (5 ml) having suspended therein 0.05 g of sodium hydride (purity: 55%). After standing for 20 minutes, the solution was added with 0.09 g of 2-chloromethylpyridine hydrochloride and stirred for 4 hours. Then N,N-dimethylformamide was distilled off and the residue was extracted with ethyl acetate by adding water. The extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off to obtain a crude product. This product was purified by preparative thin-layer chromatography using hexane/ethyl acetate (2:3) as developing solvent to obtain 0.09 g of the objective compound as pale yellow crystals.

Workup

  1. distillationThen N,N-dimethylformamide was distilled off
  2. extractionthe residue was extracted with ethyl acetate
  3. additionby adding water
  4. washThe extract was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationethyl acetate was distilled off
  7. customto obtain a crude product
  8. customThis product was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-74559945ccdc44a18e10e3821690c738
Source dataset
uspto-grants-1992_01
Patent number
US05084084

Reaction notes

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