Water → HCID 54085131, compound

HRID 2187090Notes

Reaction equation

HRID 2187090 reaction equation
[H-].[K+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([C:14]1[O:19][CH2:18][CH2:17][O:16][N:15]=1)=[CH:11][O:12][CH3:13].[O:20]([C:27]1[C:32]([F:33])=[C:31](F)[N:30]=[CH:29][N:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[O:20]([C:27]1[C:32]([F:33])=[C:31]([O:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:10]([C:14]2[O:19][CH2:18][CH2:17][O:16][N:15]=2)=[CH:11][O:12][CH3:13])[N:30]=[CH:29][N:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 82127Potassium hydrideHCID 158696744,5-Difluoro-6-phenoxypyrimidineHCID 54404573HCID 54404573, compound

Product 1

HCID 54085131HCID 54085131, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

0.119 g of potassium hydride (60% suspension in mineral oil) is added to a solution of 0.7 g (0.00298 mol) of 3-[1-(2-hydroxyphenyl)-2-methoxyethen-1-yl]-5,6-dihydro-1,4,2-dioxazine and 0.6 g (0.00288 mol) of 4-phenoxy-5,6-difluoro-pyrimidine in 10 ml of dimethylformamide at 0° C., and the mixture is then stirred for 12 hours at 20° C. The reaction mixture is poured into water and extracted using ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed on silica gel using cyclohexane/ethyl acetate (1:1). 0.4 g (82% of theory) of 3-{1-[2-(4-phenoxy-5-fluoropyrimid-6-yloxy)-phenyl]-2-methoxyethen-1-yl}-5,6-dihydro-1,4,2-dioxazine is obtained.

Workup

  1. extractionextracted
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-30619bea52e2474dae840698ff2de21d
Source dataset
uspto-grants-2002_06
Patent number
US06407233B1

Reaction notes

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