Methyl chloroformate → 4H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-(2,2-dimethylpropyl)-6-methyl-4-oxo-
Reaction equation
[CH3:1][C:2]1[N:7]2[C:8](=[O:15])[C:9]([C:12]([OH:14])=O)=[CH:10][N:11]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OC)=O.[CH2:28]([NH2:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>C(Cl)(Cl)Cl>[CH2:28]([NH:33][C:12]([C:9]1[C:8](=[O:15])[N:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]2=[N:11][CH:10]=1)=[O:14])[C:29]([CH3:32])([CH3:31])[CH3:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture containing 8.16 g (0.04 mole) of 6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and 6.2 ml (0.044 mol) of triethylamine in 240 ml of chloroform is cooled below -10° C. by ice-salt. A solution of 3.25 ml (0.04 mol) of methyl chloroformate in 20 ml of chloroform is dropped to the above solution at -16° C. during 10 minutes. After stirring for 5 minutes, 3.83 g (0.044 mol) of neopentylamine dissolved in 10 ml of chloroform are dropped to the above solution at -10° C. during 5 minutes. After stirring at -10° C. for 1 hour, the reaction mixture is washed 3 times with 80 ml of 5% sodium hydrogen carbonate solution each and then 3 times with 80 ml of water each. The organic phase is dried over anhydrous sodium sulfate and then evaporated to give 6.8 g (62.2%) of the named product as yellow crystals after recrystallization from ethanol, m.p.: 191°-194° C.
Workup
- additionare dropped to the above solution at -10° C. during 5 minutes
- stirringAfter stirring at -10° C. for 1 hour
- washthe reaction mixture is washed 3 times with 80 ml of 5% sodium hydrogen carbonate solution each and then 3 times with 80 ml of water each
- dry with materialThe organic phase is dried over anhydrous sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-6030c5ec93f640cdae1a81affecf2a54
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387588
Reaction notes
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