Triethylamine → 4H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-(1,1-dimethylpropyl)-6-methyl-4-oxo-

HRID 1655911Notes

Reaction equation

HRID 1655911 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(OCC)=O.[C:29]([NH2:34])([CH2:32][CH3:33])([CH3:31])[CH3:30]>C(Cl)(Cl)Cl>[C:29]([NH:34][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])([CH2:32][CH3:33])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 689862-Butanamine, 2-methyl-HCID 2084164H-Pyrido(1,2-a)pyrimidine-3-carboxylic acid, 6-methyl-4-oxo-

Product 1

HCID 30792824H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-(1,1-dimethylpropyl)-6-methyl-4-oxo-Yield 54%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 8.16 g (0.04 mol) 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 4 ml (0.042 mol) of ethyl chloroformate in 20 ml of chloroform is dropped to the above mixture at a temperature between -12° C. and -17° C. during 15 minutes. After stirring for 5 minutes, 3.84 g (0.044 mol) of tert.-pentylamine dissolved in 40 ml of chloroform are dropped to the above solution at the same temperature during 15 minutes. The reaction mixture is stirred for 1 hour at about -10° C. and then allowed to stand overnight under cooling by ice. For working up, the reaction mixture is washed 3 times with 50 ml of 5% sodium hydrogen carbonate solution each and then 3 times with 50 ml of water each. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated. The residue slowly becomes crystalline to give 5.9 g (54%) of the named compound, m.p. 87°-89° C. after recrystallization from ethanol.

Workup

  1. additionare dropped to the above solution at the same temperature during 15 minutes
  2. stirringThe reaction mixture is stirred for 1 hour at about -10° C.
  3. waitto stand overnight
  4. temperatureunder cooling by ice
  5. washthe reaction mixture is washed 3 times with 50 ml of 5% sodium hydrogen carbonate solution each and then 3 times with 50 ml of water each
  6. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-bf15934558ef4ed692efd77014e939c4
Source dataset
uspto-grants-1993_10
Patent number
US05252572

Reaction notes

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