Reaktion #1550426

Reaktionsgleichung

6-chloro-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

sodium thiomethoxide

→

Compound 26

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

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe methanol was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in 100 mL of ethyl acetate
3. 3
   Waschenwashed three times with 50 mL of 1M sodium hydroxide
4. 4
   TrocknenThe organic layer was dried over MgSO4
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto yield 2.6 g crude product

Vorschrift

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).

Quelle