Phenyl chloroformate → 2-Amino-4-difluoromethoxy-6-methyl-pyrimidine hydrochloride

HRID 2309162Notes

Reaction equation

HRID 2309162 reaction equation
[Cl:1]C(OC1C=CC=CC=1)=O.[NH2:11][C:12]1[N:17]=[C:16]([O:18][CH:19]([F:21])[F:20])[CH:15]=[C:14]([CH3:22])[N:13]=1>CN(C)C1C=CN=CC=1.O1CCCC1.C(OCC)(=O)C>[ClH:1].[NH2:11][C:12]1[N:17]=[C:16]([O:18][CH:19]([F:21])[F:20])[CH:15]=[C:14]([CH3:22])[N:13]=1

Participants

6

Reactant 2

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

Product 1

HCID 201856952-Amino-4-difluoromethoxy-6-methyl-pyrimidine hydrochlorideYield 58.6%

Reagents, catalysts & solvents 3

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

Procedure

3.9 g (0.025 mol) of phenyl chloroformate and 0.05 g of 4-dimethylamino-pyridine are added in succession to a solution of 9.0 g (0.05 mol) of 2-amino-4-difluoromethoxy-6-methyl-pyrimidine in 30 ml of absolute tetrahydrofuran. The solution is stirred at 20°-25° C. for 24 hours and the reaction mixture is then diluted with 250 ml of ethyl acetate and the precipitate is separated off. 3.1 g of 2-amino-4-difluoromethoxy-6-methyl-pyrimidine hydrochloride of melting point 204°-205° C. (decomposition) are thus obtained. To remove the residual starting material, the filtrate is eluted over a column containing the ion exchanger I® (MERCK), and the eluate is dried over sodium sulfate and evaporated. 4.0 g of 2-phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidine are obtained as the crude product in the form of a viscous oil. After crystallisation, the product has a melting point of 56°-58° C.

Workup

  1. customthe precipitate is separated off

Sources & evidence

ORD record
ord-06d51ba687ed434b80133160dd47d04c
Source dataset
uspto-grants-1987_09
Patent number
US04693741

Reaction notes

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