Malonic Acid → Ethyl 3-(6-methyl-3-pyridyl)propionate
Reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH3:13][C:14]1N=CC(C=O)=CC=1.C(O)(=O)CC(O)=O.[H][H]>N1C=CC=CC=1.N1CCCCC1.[Pd]>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
3-(6-Methyl-3-pyridyl)propenoic acid, m.p. 213.5-215.5°, was prepared by reacting 6-methylpyridine-3-carboxaldehyde with malonic acid in pyridine with piperidine catalyst, and was converted into the corresponding ethyl ester m.p. 36°-37° which was reduced with hydrogen and palladium-on-charcoal catalyst to give ethyl 3-(6-methyl-3-pyridyl)-propionate (oil). This ester was reacted with sodium and ethyl formate and the product treated with thiourea to give 5-(6-methyl-3-pyridylmethyl)-2-thiouracil m.p. 240°-241° which was alkylated with methyl iodide in the presence of sodium hydroxide at 70° to give 5-(6-methyl-3-pyridylmethyl)-2-methylthio-4-pyrimidone, m.p. 197°-198.5°.
Sources & evidence
- ORD record
- ord-e18a9497d06b476c944cdc5afc2b2e64
- Source dataset
- uspto-grants-1985_12
- Patent number
- US04558128
Reaction notes
Loading…