Ethyl benzoate → 2-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-phenylethan-1-one

HRID 397371

Reaction equation

HRID 397371 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=1.[C:20](OCC)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[CH3:19][S:18][C:14]1[N:13]=[C:12]([CH2:11][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:27])[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 7165Ethyl benzoateHCID 8212614-Methyl-2-(methylsulfanyl)pyrimidineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 129858292-[2-(Methylsulfanyl)pyrimidin-4-yl]-1-phenylethan-1-oneYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

86 ml (86 mmoles) of 1.0 M sodium bis(trimethylsilyl)amide in tetrahydrofuran was added drop-wise by addition funnel to a solution of 6.03 g (43 mmoles) 4-methyl-2-(methylthio)pyrimidine and 6.46 g (43 mmoles) ethyl benzoate in 86 ml tetrahydrofuran under a nitrogen atmosphere. After 2 hours the reaction was quenched with saturated ammonium chloride solution. Most of the tetrahydrofuran was removed in vacuo. The residue was diluted with 400 ml ethyl acetate and 200 ml water. The organic layer was separated and washed 2×100 ml saturated sodium chloride solution, separated, dried over Na2SO4, filtered, and concentrated in vacuo to give 10.45 g (42.77 mmoles) of 2-[2-(methyl thio)pyrimidin-4-yl]-1-phenyle thanone as a viscous red-brown oil that solidified upon standing. MH+=244.9.

Workup

  1. customAfter 2 hours the reaction was quenched with saturated ammonium chloride solution
  2. customMost of the tetrahydrofuran was removed in vacuo
  3. additionThe residue was diluted with 400 ml ethyl acetate and 200 ml water
  4. customThe organic layer was separated
  5. washwashed 2×100 ml saturated sodium chloride solution
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b5de7a632a44f69a9fe8f875b648dd4
Source dataset
uspto-grants-2003_08
Patent number
US06610697B1

Linked notes

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