Dimethylformamide dimethyl acetal → 4-Methyl-2-(methylsulfanyl)pyrimidine

HRID 394470Notes

Reaction equation

HRID 394470 reaction equation
Cl.[SH:2][C:3]1[N:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1.[CH3:10]OC(OC)N(C)C.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[CH3:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:10])[N:8]=1

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 81531DiisopropylethylamineHCID 1784286872-Mercapto-4-methylpyrimidine hydrochloride

Product 1

HCID 8212614-Methyl-2-(methylsulfanyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Mercapto-4-methylpyrimidine hydrochloride (100 g, 617 mmol), dimethylformamide dimethylacetal (100 mL, 754 mmol), diisopropylethylamine (161 mL, 926 mmol) and toluene (200 mL) were combined under argon. The resulting solution was heated to reflux for 4 h. The solvent was removed in vacuo and water and sodium bisulfate were added. The resulting mixture was extracted with ether (3×100 mL). The combined organic extracts were washed with brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford an oil. Vacuum distillation gave Compound 2 as a liquid: 70.5 g, (504 mmol, 82%)

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was removed in vacuo and water and sodium bisulfate
  4. additionwere added
  5. extractionThe resulting mixture was extracted with ether (3×100 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customto afford an oil
  10. distillationVacuum distillation

Sources & evidence

ORD record
ord-4be6c7cd8f854b33b016eec538774b78
Source dataset
uspto-grants-2003_08
Patent number
US06602872B1

Reaction notes

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