Tert-Butylamine → 4H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-(1,1-dimethylethyl)-6-methyl-4-oxo-

HRID 467008Notes

Reaction equation

HRID 467008 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.[C:28]([NH2:32])([CH3:31])([CH3:30])[CH3:29]>C(Cl)(Cl)Cl>[C:28]([NH:32][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])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 2084164H-Pyrido(1,2-a)pyrimidine-3-carboxylic acid, 6-methyl-4-oxo-

Product 1

HCID 30792764H-Pyrido(1,2-a)pyrimidine-3-carboxamide, N-(1,1-dimethylethyl)-6-methyl-4-oxo-Yield 74.7%

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 mol) 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 -20° C. during 20 minutes. After stirring for 5 minutes, 6.47 g (0.088 mol) of tert.-butylamine dissolved in 80 ml of chloroform are dropped to the above solution at a temperature between -18° C. and -20° C. during 50 minutes. The reaction mixture is stirred for 1 hour at the same temperature and then let to stand in the refrigerator overnight. For working up, the mixture is washed 3 times with 150 ml of 5% sodium hydrogen carbonate each and then 3 times with 150 ml of water each. The organic phase is dried over anhydrous sodium sulfate and evaporated to give 15.5 g (74.7%) of the named product as light beige crystals after recrystallization from ethanol, m.p.: 164°-166° C.

Workup

  1. additionare dropped to the above solution at a temperature between -18° C. and -20° C. during 50 minutes
  2. stirringThe reaction mixture is stirred for 1 hour at the same temperature
  3. customto stand in the refrigerator overnight
  4. washthe mixture is washed 3 times with 150 ml of 5% sodium hydrogen carbonate each and then 3 times with 150 ml of water each
  5. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-aba1a9117c1946619f2f0f6eece03abe
Source dataset
uspto-grants-1992_10
Patent number
US05158951

Reaction notes

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