Diethyl Ether → Ethyl 5-hydroxy-2-(methylthio)-7-oxo-8-propyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate
Reaction equation
C(O[C:4]([C:6]1[C:7]([NH:14][CH2:15][CH2:16][CH3:17])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])C.C([CH:20]([C:24](Cl)=[O:25])[C:21](Cl)=[O:22])C.[CH2:27]([O:29]CC)[CH3:28]>>[CH2:27]([O:29][C:24]([C:20]1[C:21](=[O:22])[N:14]([CH2:15][CH2:16][CH3:17])[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[C:4]=1[OH:5])=[O:25])[CH3:28]Participants
Procedure
To a solution of 12.8 g. (0.05 mole) of 2-methylthio-4-propylamino-5-pyrimidine carboxylic acid ethyl ester in 100 ml. of anhydrous diethyl ether was added 0.75 g. (0.025 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 4 hours and was filtered. The filtrate was evaporated in a rotary evaporator and the residue was dissolved in 15 ml. of ethanol and this solution was added to a solution of 1.15 g. (0.05 g atom) of sodium in 100 ml. of ethanol. After stirring at room temperature for 5 minutes, the mixture was diluted with water to the cloudy point and was acidified with conc. hydrochloric acid. The precipitate which formed was collected, air dried and was recrystallized from ethyl acetate to give 0.2 g. of title product--m.p. 130°-133° C.
Workup
- filtrationwas filtered
- customThe filtrate was evaporated in a rotary evaporator
- dissolutionthe residue was dissolved in 15 ml
- additionof ethanol and this solution was added to a solution of 1.15 g
- stirringAfter stirring at room temperature for 5 minutes
- additionthe mixture was diluted with water to the cloudy point
- customThe precipitate which formed
- customwas collected
- customair dried
- customwas recrystallized from ethyl acetate
- customto give 0.2 g
Sources & evidence
- ORD record
- ord-2470a28ab6234cb79ccc3bf0a0d3cfb0
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04215216
Reaction notes
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