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

HRID 273702Notes

Reaction equation

HRID 273702 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.[CH:28]([NH2:31])([CH3:30])[CH3:29]>C(Cl)(Cl)Cl>[CH:28]([NH:31][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])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 2084164H-Pyrido(1,2-a)pyrimidine-3-carboxylic acid, 6-methyl-4-oxo-

Product 1

HCID 30792744H-Pyrido(1,2-a)pyrimidine-3-carboxamide, 6-methyl-N-(1-methylethyl)-4-oxo-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture containing 16.32 g (0.08 mol) of 6-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and 12.4 ml (0.088 mole) of triethylamine in 480 ml of chloroform is cooled below -10° C. by ice-salt. A solution of 6.5 ml (0.08 mol) of methyl chloroformate in 40 ml of chloroform is dropped to the above mixture at a temperature between -12° C. and -16° C. during 30 minutes. After stirring for 5 minutes, 5.2 g (0.088 mol) of isopropylamine dissolved in 80 ml of chloroform are dropped to the above solution at -15° C. during 40 minutes, then the mixture is stirred for 1 hour at the same temperature and thereafter maintained under cooling by ice.

Workup

  1. additionare dropped to the above solution at -15° C. during 40 minutes
  2. stirringthe mixture is stirred for 1 hour at the same temperature
  3. temperaturemaintained
  4. temperatureunder cooling by ice

Sources & evidence

ORD record
ord-4b5e2e90dd134d439eadc73fbe74aa4a
Source dataset
uspto-grants-1995_02
Patent number
US05387588

Reaction notes

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