4,6-Dichloro-2-methylpyrimidine → 4-Chloro-2-methyl-6-(methylthio)pyrimidine

HRID 1621648Notes

Reaction equation

HRID 1621648 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][S-:11].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([S:11][CH3:10])[N:5]=[C:4]([CH3:9])[N:3]=1

Participants

4

Reactant 2

HCID 2349974,6-Dichloro-2-methylpyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 569244304-Chloro-2-methyl-6-(methylthio)pyrimidineYield 44.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4,6-dichloro-2-methylpyrimidine (11.5 g, 70.6 mmol, Aldrich) and sodium methanethiolate (5.93 g, 85 mmol, Aldrich) in toluene (50 mL) was stirred at 25° C. for 24 h. The reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc, washed with brine, and dried over Na2SO4. The crude product was purified by recrystallization from hexane to give 4-chloro-2-methyl-6-(methylthio)pyrimidine (5.5 g, 31.5 mmol, 44.6% yield) as white crystals. 1H NMR (400 MHz, CDCl3) δ 7.01 (s, 1H); 2.64 (s, 3H); 2.56 (s, 3H). m/z (ESI, +ve ion) 175 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by recrystallization from hexane

Sources & evidence

ORD record
ord-2224492431744099bd408204f15a5fbe
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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