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

HRID 342685

Reaction equation

HRID 342685 reaction equation
[SH:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.Cl.[CH:10](N(C(C)C)CC)(C)C.COC(OC)N(C)C>C1(C)C=CC=CC=1>[CH3:10][S:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineYield 84.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2-mercapto-4-methylpyrimidine·HCl (50.0 g, 0.307 mole) in toluene (750 mL), under argon, was added diisopropylethylamine (80.0 mL, 0.461 mole) followed by N,N-dimethylformamide dimethyl acetal (100 mL) and the mixture heated to reflux for 4 hours. Upon cooling, the reaction was concentrated in vacuo to an oil, dissolved in ether (400 mL), and washed with water (2×50 mL). The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to an oil which was vacuum distilled to give 2-methylthio-4-methylpyrimidine (36.4 g) as an oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 hours
  3. temperatureUpon cooling
  4. concentrationthe reaction was concentrated in vacuo to an oil
  5. dissolutiondissolved in ether (400 mL)
  6. washwashed with water (2×50 mL)
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to an oil which
  11. distillationdistilled

Sources & evidence

ORD record
ord-a19ceaf028184881a3776d4a7655c208
Source dataset
uspto-grants-1999_01
Patent number
US05859041

Linked notes

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