Reaction equation
C(O[C:4]([C:6]1[C:7]([NH:14][CH3:15])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])C.C([CH:18]([C:22](Cl)=[O:23])[C:19](Cl)=[O:20])C.[CH2:25]([O:27]CC)[CH3:26]>>[CH2:25]([O:27][C:22]([C:18]1[C:19](=[O:20])[N:14]([CH3:15])[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[C:4]=1[OH:5])=[O:23])[CH3:26]Participants
Procedure
To a solution of 4.54 g. (0.02 mole) of 4-methylamino-2-methylthio-5-pyrimidine carboxylic acid ethyl ester in 100 ml. of anhydrous diethyl ether was added 1.5 g. (0.01 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 1 hour. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was triturated with a few ml. of diethyl ether and was filtered. The filtrate was evaporated and the residue was dissolved in 10 ml. of ethanol. This solution was added to a solution of 0.37 g. (0.015 g atom) of sodium in 20 ml. of ethanol. The mixture was stirred at room temperature for 10 minutes. The mixture was diluted with water and was acidified with glacial acetic acid. The precipitate which formed was collected, air dried and was recrystallized from ethanol to afford 0.4 g. of title product--m.p. 166°-168° C.
Workup
- filtrationThe mixture was filtered
- customthe filtrate was evaporated in a rotary evaporator
- customThe residue was triturated with a few ml
- filtrationof diethyl ether and was filtered
- customThe filtrate was evaporated
- dissolutionthe residue was dissolved in 10 ml
- additionThis solution was added to a solution of 0.37 g
- stirringThe mixture was stirred at room temperature for 10 minutes
- additionThe mixture was diluted with water
- customThe precipitate which formed
- customwas collected
- customair dried
- customwas recrystallized from ethanol
- customto afford 0.4 g
Sources & evidence
- ORD record
- ord-8ea44cdbd52c4d0a8d0d518502115609
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04236004
Linked notes
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