Pyridine → 4-Amino-6-(3,3-dimethylbutyramido)quinazoline

HRID 354855Notes

Reaction equation

HRID 354855 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[N:6]=[CH:5][N:4]=1.C(N(CCC)CCC)CC.N1C=CC=CC=1.[CH3:30][C:31]([CH3:37])([CH3:36])[CH2:32][C:33](Cl)=[O:34]>C(Cl)(Cl)Cl.CO.CO.C(Cl)(Cl)Cl>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:33](=[O:34])[CH2:32][C:31]([CH3:37])([CH3:36])[CH3:30])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 7616TripropylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 202660864,6-Diaminoquinazoline hydrochloride

Product 1

HCID 130604604-Amino-6-(3,3-dimethylbutyramido)quinazolineYield 64.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 21584188Chloroform methanolSolvent

Procedure

To a mixture of 4,6-diaminoquinazoline hydrochloride (10.0 g), tripropylamine (17.61 g) and dry pyridine (100 ml) was added dropwise during 35 minutes 3,3-dimethylbutyryl chloride (10.34 g) under ice-cooling. The reaction mixture was stirred for 2 hours at the same temperature. To the resultant mixture was added ice-water. The mixture was stirred for 5 minutes and then concentrated under reduced pressure. To the residue was added water and sodium hydrogen carbonate (13.0 g) little by little to give precipitates, which were separated by filtration, washed with water and dried. Thus obtained crude crystals were dissolved in a mixture of chloroform and methanol under heating. After insoluble materials were removed by filtration, the filtrate was concentrated under reduced pressure to give a residue, which was suspended in 5% methanol-chloroform solution (70 ml). After stirring under heating, the suspension was filtered to give crystalline 4-amino-6-(3,3-dimethylbutyramido)quinazoline (8.5 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 5 minutes
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added water and sodium hydrogen carbonate (13.0 g) little by little
  5. customto give
  6. customprecipitates
  7. customwhich were separated by filtration
  8. washwashed with water
  9. customdried
  10. customThus obtained crude crystals
  11. temperatureunder heating
  12. customAfter insoluble materials were removed by filtration
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customto give a residue, which
  15. stirringAfter stirring
  16. temperatureunder heating
  17. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-f627221b509d4f7a9ea8877654c68a9a
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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