Phenyl chloroformate → 2-Phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidine

HRID 1633346Notes

Reaction equation

HRID 1633346 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH:9]([F:11])[F:10])[CH:5]=[C:4]([CH3:12])[N:3]=1.[C:13]1([O:19][C:20](Cl)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[O:19]([C:20]([NH:1][C:2]1[N:7]=[C:6]([O:8][CH:9]([F:11])[F:10])[CH:5]=[C:4]([CH3:12])[N:3]=1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 15891Phenyl chloroformateHCID 28173904-(Difluoromethoxy)-6-methylpyrimidin-2-amine

Product 1

HCID 221041722-Phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidineYield 54.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 9.0 g of 2-amino-4-difluoromethoxy-6-methyl-pyrimidine in 30 ml of absolute tetrahydrofuran are added successively 3.9 g of chloroformic acid-phenyl ester and 0.05 g of 4-dimethylamino-pyridine. After the solution has been stirred at 20° to 25° C. for 24 hours, the reaction mixture is diluted with 250 ml of ethyl acetate, and the occurring precipitate is separated. There are thus obtained 3.1 g of 2-amino-4-difluoromethoxy-6-methyl-pyrimidine hydrochloride, m.p. 204° to 205° C. (decomposition). In order to remove the residual starting material, the filtrate is eluted through an acid with ion-exchanger I®(MERCK), dried over sodium sulfate and concentrated by evaporation to thus obtain as crude product, in the form of a viscous oil, 4.0 g of 2-phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidine (compound No. 2.28), which melts at 56° to 58° C. after crystallisation;

Workup

  1. customthe occurring precipitate is separated
  2. customIn order to remove the
  3. washthe filtrate is eluted through an acid with ion-exchanger I®(MERCK)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4e3ab81a099a4223a23956f2d1ca5b5d
Source dataset
uspto-grants-1984_10
Patent number
US04480101

Reaction notes

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