Potassium Fluoride → 2-Chloro-4-chloromethyl-6-fluoro-pyrimidine

HRID 1380844Notes

Reaction equation

HRID 1380844 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[C:7](Cl)[N:6]=[C:5]([Cl:10])[N:4]=1.[F-:11].[K+]>S1(CCCC1)(=O)=O>[Cl:10][C:5]1[N:4]=[C:3]([CH2:2][Cl:1])[CH:8]=[C:7]([F:11])[N:6]=1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 150017782,4-Dichloro-6-(chloromethyl)pyrimidine

Product 1

HCID 233246642-Chloro-4-chloromethyl-6-fluoro-pyrimidine

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
0 °C

Procedure

5 g (0.027 mol) of 4-chloromethyl-2,6-dichloro-pyrimidine (see Examples 73 and 92) and 3.3 g (0.056 mol) of anhydrous potassium fluoride in 8 ml of sulpholane are heated at 140° C. for 24 hours. The mixture is then cooled to 0° C. and filtered over silica gel using diethyl ether/n-hexane (1:4). After removing the solvent by evaporation there is obtained 2-chloro-4-chloromethyl-6-fluoro-pyrimidine in the form of a yellow oil, 1H-NMR (CDCl3): 4.70 (s, CH2Cl), 7.30 (d, JFH =2 Hz, H).

Workup

  1. filtrationfiltered over silica gel
  2. customAfter removing the solvent
  3. customby evaporation

Sources & evidence

ORD record
ord-fedbbb45af2d4b0fafd4ccf51df4301d
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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