Reaction #1547

Reaction equation

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

sodium hydroxide

→

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

Yield 53.2%

Solvents

ethanol

THF

Conditions

Workup

1. 1
   Otherto remove the bulk of the organic solvents
2. 2
   workup.ADDITIONThe residue was diluted with 50 mL of 5% aqueous sodium hydroxide
3. 3
   Washwashed with 100 mL of ether
4. 4
   Extractionextracted with two 100 mL portions of ethyl acetate
5. 5
   WashThe combined ethyl acetate extracts were washed with 50 mL of brine
6. 6
   Dryingdried over MgSO4
7. 7
   Concentrationconcentrated

Procedure

To a solution of 1.81 g (6.1 mmol) of 6-ethoxycarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone in 100 mL of ethanol and 50 mL of THF was added 50 mL of 5% aqueous sodium hydroxide. The mixture was stirred at room temperature for 24 h and rotovapped to remove the bulk of the organic solvents. The residue was diluted with 50 mL of 5% aqueous sodium hydroxide and washed with 100 mL of ether. The aqueous phase was acidified with concentrated hydrochloric acid and extracted with two 100 mL portions of ethyl acetate. The combined ethyl acetate extracts were washed with 50 mL of brine, dried over MgSO4 and concentrated to leave 0.87 g (53%) of crude 6-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone as a brown oil.

Source