1,3,3,3-Tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propene → 4-Fluoro-6-methoxy-5-(trifluoromethyl)pyrimidine

HRID 709940Notes

Reaction equation

HRID 709940 reaction equation
[F:1][C:2](F)(F)[C:3]([C:8]([F:11])([F:10])[F:9])=[C:4](F)[O:5][CH3:6].C(O)(=O)C.[CH:18]([NH2:20])=[NH:19].[OH-].[Na+]>O.ClCCl>[F:1][C:2]1[C:3]([C:8]([F:11])([F:10])[F:9])=[C:4]([O:5][CH3:6])[N:20]=[CH:18][N:19]=1

Participants

6

Reactant 3

HCID 96721,3,3,3-Tetrafluoro-1-methoxy-2-(trifluoromethyl)-1-propeneHCID 14798Sodium HydroxideHCID 160693Formamidine acetate

Product 1

HCID 584392514-Fluoro-6-methoxy-5-(trifluoromethyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a rapidly stirred mixture of 1,1,1,3-tetrafluoro-2-(trifluoromethyl)-4-oxapent-2-ene (N-1) (10.0 g, 47.15 mmol) and formamidine acetate (7.37 g, 70.73 mmol) in a mixture of water (50 mL) and dichloromethane (50 mL) at 0° C., a solution of sodium hydroxide (7.54 g, 189 mmol) in water (40 mL) is added dropwise and the resulting mixture is stirred for 30 min after complete addition. The dichloromethane layer is separated, washed with 1M aqueous HCl solution and water, dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo to afford 4-fluoro-6-methoxy-5-(trifluoromethyl)pyrimidine (N-2) as a yellow solid. The product is used directly in the next step without further purification.

Workup

  1. additionafter complete addition
  2. customThe dichloromethane layer is separated
  3. washwashed with 1M aqueous HCl solution and water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-de83daed5cea4bec985947965cf126b8
Source dataset
uspto-grants-2015_11
Patent number
US09181221B2

Reaction notes

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