Sodium methanethiolate → 5-methyl-2-phenyl-3-propargyl-6-methylthio-4(3H)-pyrimidinone

HRID 1463244

Reaction equation

HRID 1463244 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([CH2:14][C:15]#[CH:16])[C:4](=[O:17])[C:3]=1[CH3:18].[CH3:19][S-:20].[Na+]>CO>[CH3:18][C:3]1[C:4](=[O:17])[N:5]([CH2:14][C:15]#[CH:16])[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:7][C:2]=1[S:20][CH3:19]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 196907006-chloro-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

Product 1

HCID 196907125-methyl-2-phenyl-3-propargyl-6-methylthio-4(3H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.5 g (9.67 mmol) of 6-chloro-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone in 100 mL of methanol, was added 0.8 g (11.4 mmol) sodium thiomethoxide and the reaction was stirred at room temperature for 4 days. The methanol was evaporated and the residue was dissolved in 100 mL of ethyl acetate, then washed three times with 50 mL of 1M sodium hydroxide followed by one time with 50 mL of brine. The organic layer was dried over MgSO4 and concentrated to yield 2.6 g crude product. Flash column chromatography on silica gel (100% methylene chloride) afforded 5-methyl-2-phenyl-3-propargyl-6-thiomethyl-4(3H)-pyrimidinone (Compound 26) as a white solid. 1H-NMR (CDCl3) δ2.1 (3H, s); 2.35 (1H, t); 2.5 (3H, s); 4.55 (2H, d); 7.5 (3H, m); 7.7 (2H, m).

Workup

  1. customThe methanol was evaporated
  2. dissolutionthe residue was dissolved in 100 mL of ethyl acetate
  3. washwashed three times with 50 mL of 1M sodium hydroxide
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customto yield 2.6 g crude product

Sources & evidence

ORD record
ord-377906cb16a849deaf5e8ad5fe6ba6e2
Source dataset
uspto-grants-1994_04
Patent number
US05300477

Linked notes

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