Methyl chloroformate → Pyrrolidine, 1-((6-methyl-4-oxo-4H-pyrido(1,2-a)pyrimidin-3-yl)carbonyl)-

HRID 273722Notes

Reaction equation

HRID 273722 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.[CH2:16]([N:18](CC)[CH2:19][CH3:20])[CH3:17].ClC(OC)=O.N1CCCC1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:7]2[C:8](=[O:15])[C:9]([C:12]([N:18]3[CH2:19][CH2:20][CH2:17][CH2:16]3)=[O:14])=[CH:10][N:11]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 31268PyrrolidineHCID 2084164H-Pyrido(1,2-a)pyrimidine-3-carboxylic acid, 6-methyl-4-oxo-

Product 1

HCID 3079297Pyrrolidine, 1-((6-methyl-4-oxo-4H-pyrido(1,2-a)pyrimidin-3-yl)carbonyl)-Yield 32.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 20.4 g (0.1 mol) of 6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and 15.5 ml (0.11 mol) of triethylamine in 600 ml of chloroform is cooled below -10° C. by ice-salt. A solution of 10 ml (0.1 mol) of methyl chloroformate dissolved in 50 ml of chloroform is dropped to the above mixture at -10° C. during 30 to 35 minutes. After stirring for 20 minutes, 9 g (0.11 mol) of pyrrolidine dissolved in 100 ml of chloroform are dropped to the above solution at a temperature between -5° C. and -8° C. during 1 hour. The reaction mixture is stirred at the same temperature for 1 hour, then allowed to stand overnight under cooling by ice. For working up, the reaction mixture is washed 3 times with 400 ml of 5% sodium hydrogen carbonate solution each, then 3 times with 400 ml of water each. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated. After suspending the oily residue in petroleum ether, 8.3 g (32.3%) of the named compound are obtained, which forms yellow crystals after recrystallization from ethanol, m.p.: 132°-134° C.

Workup

  1. additionis dropped to the above mixture at -10° C. during 30 to 35 minutes
  2. additionare dropped to the above solution at a temperature between -5° C. and -8° C. during 1 hour
  3. stirringThe reaction mixture is stirred at the same temperature for 1 hour
  4. waitto stand overnight
  5. temperatureunder cooling by ice
  6. washthe reaction mixture is washed 3 times with 400 ml of 5% sodium hydrogen carbonate solution each, then 3 times with 400 ml of water each
  7. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-5ea0fb8f30a44c77b62a84a1e1de4de3
Source dataset
uspto-grants-1995_02
Patent number
US05387588

Reaction notes

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