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

HRID 1453280Notes

Reaction equation

HRID 1453280 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-methylpyrimidine 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. 1H NMR (CDCl3, 300 MHz) δ, ppm: 2.46 (s, 3H), 2.56 (s, 3H), 6.82 (d, J=5 Hz, 1H,), 8.37 (d, J=5 Hz 1H).

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-95602dcc29974a36b2e996c299f5c853
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

Loading…