Hydrazine hydrate (1:1) → HCID 57758598, compound

HRID 229401Notes

Reaction equation

HRID 229401 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9](S(C)(=O)=O)=[N:10][CH:11]=1)=[O:5])[CH3:2].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[OH:25].CC[O-].[Na+].O.[NH2:31][NH2:32]>CC(OC)(C)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:31][NH2:32])=[N:8][C:9]([O:25][C:19]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=2[F:17])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 1230512,4-DifluorophenolHCID 2723922Sodium ethoxideHCID 577586014-Chloro-2-methanesulfinyl-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 57758598HCID 57758598, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a suspension of 4-chloro-2-methanesulfonyl-pyrimidine-5-carboxylic acid ethyl ester (12.8 g) and 2,4-difluorophenol (6.42 g) in MTBE (100 mL) was added a solution of NaOEt (3.87 g) in water (64 mL) at 0° C. The reaction was warmed to room temperature and stirred for one hour. The mixture was then added into a solution of hydrazine hydrate (4.8 g) in MTBE (25 mL) at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for four hours, then quenched by addition of water and extracted with methylene chloride. The combined organic layers were dried with MgSO4, filtered and concentrated under reduced pressure to give 2-(2,4-difluoro-phenoxy)-4-hydrazino-pyrimidine-5-carboxylic acid ethyl ester (8.0 g).

Workup

  1. temperatureThe reaction mixture was slowly warmed to room temperature
  2. stirringstirred for four hours
  3. customquenched by addition of water
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8488dfdcf7814c829f04751e21b33793
Source dataset
uspto-grants-2009_07
Patent number
US07563800B2

Reaction notes

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