Water → HCID 2848522, compound

HRID 1843080Notes

Reaction equation

HRID 1843080 reaction equation
F[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[N:5]=[C:4]([CH3:19])[N:3]=1.[C-:20]#[N:21].[Na+].O.C(OCC)(=O)C>C(#N)C>[CH3:19][C:4]1[N:3]=[C:2]([C:20]#[N:21])[C:7]([C:8]([F:11])([F:10])[F:9])=[C:6]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium Cyanide2×HCID 111302784-Fluoro-2-methyl-6-pentafluoroethyl-5-trifluoromethylpyrimidine

Product 1

HCID 2848522HCID 2848522, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

5.0 g (16.8 mmol) of 4-fluoro-2-methyl-6-(pentafluoroethyl)-5-(trifluoromethyl)pyrimidine are dissolved in 40 ml of acetonitrile. 986 mg (20.1 mmol) of sodium cyanide are added and the reaction mixture is stirred for 18 hours at 50° C. A further 493 mg (10.7 mmol) of sodium cyanide are added and the reaction mixture is stirred under reflux for three hours. After adding 100 ml of water and 100 ml of ethyl acetate, the organic phase is separated off. The aqueous phase is extracted three times with ethyl acetate. The combined organic phases are washed twice with water and with a saturated sodium chloride solution, then dried over sodium sulphate, filtered and the solvent is removed on a rotary evaporator. This gives 4.71 g of 2-methyl-6-(pentafluoroethyl)-5-(trifluoromethyl)pyrimidine-4-carbonitrile (92%) as a dark oil.

Workup

  1. stirringthe reaction mixture is stirred
  2. temperatureunder reflux for three hours
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted three times with ethyl acetate
  5. washThe combined organic phases are washed twice with water and with a saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-72f3f6c7d9344eecaa3bbed96318bb3a
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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