Acetonitrile → 4-(Phenylsulfanyl)-6-ethyl-5-fluoropyrimidine

HRID 2384513Notes

Reaction equation

HRID 2384513 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1.C(#N)C.[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>O.ClCCl>[C:14]1([S:20][C:2]2[C:7]([F:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 167434454-Chloro-6-ethyl-5-fluoropyrimidine

Product 1

HCID 675421014-(Phenylsulfanyl)-6-ethyl-5-fluoropyrimidineYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

40 g of 4-chloro-6-ethyl-5-fluoropyrimidine was added to 400 ml of acetonitrile, and 28 ml of thiophenol was added thereto, followed by lowering the temperature to 10° C. 43.39 ml of diisopropylethylamine was added to the resulting solution, and reacted for 2 hours while maintaining the temperature at room temperature. 65 ml of dichloromethane and 200 ml of water were added to the resulting mixture to separate layer, and the resulting aqueous mixture was extracted with 200 ml of dichloromethane. The organic layer was dried over magnesium sulfate and concentrated under a reduced pressure to obtain the title compound as an oil (63.6 g, yield: 95%).

Workup

  1. additionwas added
  2. customto 10° C
  3. customreacted for 2 hours
  4. customto separate layer
  5. extractionthe resulting aqueous mixture was extracted with 200 ml of dichloromethane
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-52519844df134ab7b07fa71a8309cc65
Source dataset
uspto-grants-2012_09
Patent number
US08263769B2

Reaction notes

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