Water → HCID 21478866, compound

HRID 2292567Notes

Reaction equation

HRID 2292567 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[F:9][C:10]([F:14])([F:13])[CH2:11][OH:12].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:12][CH2:11][C:10]([F:14])([F:13])[F:9])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 709434,6-Dichloropyrimidine

Product 1

HCID 21478866HCID 21478866, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,6-dichloropyrimidine (20 g) potassium carbonate (37 g) and 2,2,2-trifluoroethanol (10.3 cm3) were stirred together at ambient temperature in dry dimethyl formamide (DMF) (130 cm3) for seven hours. The mixture was stored at ambient temperature for 60 hours before being poured into water. The product was extracted with diethyl ether and the organic layer was washed with saturated brine and dried over magnesium sulfate. Evaporation under reduced pressure afforded 4-chloro-6-(2,2,2-trifluoroethoxy)-pyrimidine as a 1:1.5 mixture with residual DMF. 1H NMR (CDCl3): δ4.79-4.89(2H,q); 6.93(1H, s); 8.61(1H,s). This was used directly in step 2.

Workup

  1. extractionThe product was extracted with diethyl ether
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-373bee2735be4186ae3d99f6b40f176f
Source dataset
uspto-grants-1997_11
Patent number
US05684011

Reaction notes

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