Methyl iodide → 4-Methyl-2-(methylsulfanyl)pyrimidine

HRID 858824Notes

Reaction equation

HRID 858824 reaction equation
[OH-].[Na+].Cl.[SH:4][C:5]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][N:6]=1.[CH3:12]I>O>[CH3:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH3:12])[N:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1784286872-Mercapto-4-methylpyrimidine hydrochloride

Product 1

HCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Based on a reported procedure (Ishizumi, K.; Kojima, A.; Antoku, F. Chem Pharm Bull 1991, 39, 2288). Sodium hydroxide (92.5 g, 2.31 mol) was added to a suspension of 2-mercapto-4-methyl pyrimidine hydrochloride (150 g, 0.93 mol) in water (1.5 L). Methyl iodide (78.9 ml, 1.39 mol) was rapidly added to the clear solution (solution temp. <20° C.). After overnight stirring, diethyl ether (400 mL), the organic layer was separated and the aqueous layer was extracted with diethyl ether (4×200 ml) all organic layers were combined, washed with 5% aq. NaOH solution (100 ml), brine (200 ml, 2 times), and dried (MgSO4), concentrated in vacuo to afford 119.3 g of crude material (95% pure by NMR) which was used in the next step without purification.

Workup

  1. customdiethyl ether (400 mL), the organic layer was separated
  2. extractionthe aqueous layer was extracted with diethyl ether (4×200 ml) all organic layers
  3. washwashed with 5% aq. NaOH solution (100 ml), brine (200 ml, 2 times)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5fcb8276a9e47cdb61ec778732811e8
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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