Hydrochloric Acid → 2-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-phenylethan-1-one

HRID 2212868Notes

Reaction equation

HRID 2212868 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[C:10](OC)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)([O-])C.[K+].Cl>O1CCCC1>[CH3:9][S:8][C:4]1[N:3]=[C:2]([CH2:1][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:17])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7150Methyl BenzoateHCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 129858292-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-phenylethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methyl-2-methylthio-pyrimidine (30 g, 0.21 mol) and methyl benzoate (30 g, 0.21 mol) is added to a solution of potassium tert-butoxide (54 g, 0.48 mol) in tetrahydrofuran (350 ml) with cooling in such a way that the reaction temperature does not exceed +20° C. After stirring the mixture for additional 20 minutes the solution is poured onto crushed ice. The resulting solution is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. Drying of the organic phase, filtering and evaporation of the solvent under reduced pressure gives the 2-(2-methylthio-pyrimidin-4-yl)-1-phenyl-ethanone in form of a mixture of tautomers.

Workup

  1. temperaturewith cooling in such a way that the reaction temperature
  2. customdoes not exceed +20° C
  3. additionis poured
  4. customonto crushed ice
  5. extractionextracted with ethyl acetate
  6. customDrying of the organic phase
  7. filtrationfiltering
  8. customevaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-acc419ad46d04b88b168267eb6664310
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

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