Ammonia → HCID 23153317, compound

HRID 492861Notes

Reaction equation

HRID 492861 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[C:11](Cl)[N:10]=[CH:9][N:8]=2)=[CH:4][C:3]=1[F:16].[NH3:17]>O1CCCC1.CO>[NH2:17][C:11]1[CH:12]=[C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([NH2:1])=[C:3]([F:16])[CH:4]=2)[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 231530834-[(6-Chloropyrimidin-4-yl)oxy]-2-fluoroaniline

Product 1

HCID 23153317HCID 23153317, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 4-(4-amino-3-fluorophenoxy)-6-chloropyrimidine (2.25 g) in tetrahydrofuran (25 ml) and a 7N ammonia solution in methanol (50 ml), the mixture was heated in a sealed tube for 3 days at 130° C. The reaction mixture was cooled to room temperature and then partitioned between ethyl acetate and 1N aqueous sodium hydroxide. The separated organic layer was washed with brine. The aqueous layer was then re-extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=1:3, then ethyl acetate) to provide the title compound (0.73 g, 35%) as a purple solid.

Workup

  1. custompartitioned between ethyl acetate and 1N aqueous sodium hydroxide
  2. washThe separated organic layer was washed with brine
  3. extractionThe aqueous layer was then re-extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-0aa99af7eb84487898b445a63438a081
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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