1,1-Dichloroethane → 4-Fluoro-6-methoxy-2-methyl-5-(trifluoromethyl)pyrimidine

HRID 1266927Notes

Reaction equation

HRID 1266927 reaction equation
[CH3:1][O:2][C:3](F)(F)[CH:4]([C:9]([F:12])([F:11])[F:10])[C:5](F)(F)[F:6].Cl.[C:16]([NH2:19])(=[NH:18])[CH3:17].ClC(Cl)C.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[F:6][C:5]1[C:4]([C:9]([F:12])([F:11])[F:10])=[C:3]([O:2][CH3:1])[N:19]=[C:16]([CH3:17])[N:18]=1

Participants

7

Reactant 4

HCID 63651,1-DichloroethaneHCID 14798Sodium HydroxideHCID 454591,1,1,3,3-Pentafluoro-3-methoxy-2-(trifluoromethyl)propaneHCID 67170Acetamidine monohydrochloride

Product 1

HCID 133793024-Fluoro-6-methoxy-2-methyl-5-(trifluoromethyl)pyrimidineYield 134.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A reaction flask was loaded with 1,1,3,3,3-pentafluoro-2-trifluoromethylpropyl methyl ether (18.1 g), acetamidine hydrochloride (11.1 g), dichloroethane (78 ml), water (78 ml), and benzyltriethylammonium chloride (0.078 g), and cooled to 0° C. with stirring. To this mixture, a 17% aqueous solution of sodium hydroxide (93 g) was dropwise added in 1.5 hours, followed by stirring for 1 hour. Thereafter, the cooling was stopped, and an organic layer was separated from the reaction mixture at room temperature and condensed to give 4-fluoro-6-methoxy-2-methyl-5-(trifluoromethyl)-pyrimidine (22 g). By GC/MS analysis, a molecular ion peak of 210 was confirmed for this compound.

Workup

  1. stirringby stirring for 1 hour
  2. customan organic layer was separated from the reaction mixture at room temperature
  3. customcondensed

Sources & evidence

ORD record
ord-579c483760d94d439732ee520895c018
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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