Pyridine → 4-Amino-6-methanesulfonamidoquinazoline

HRID 354854Notes

Reaction equation

HRID 354854 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(=O)([O-])O.[Na+].N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>CO.C(Cl)(Cl)Cl>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][S:26]([CH3:25])(=[O:28])=[O:27])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 202660864,6-Diaminoquinazoline hydrochloride

Product 1

HCID 130604594-Amino-6-methanesulfonamidoquinazolineYield 60.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4,6-diaminoquinazoline hydrochloride (1.97 g), sodium hydrogen carbonate (6.72 g) and pyridine (20 ml) was stirred under ice-cooling. To the mixture was added dropwise during 30 minutes methanesulfonyl chloride (4.58 g) under ice-cooling. The reaction mixture was stirred for an hour under ice-cooling and for 4 hours at ambient temperature. To the mixture was added ice-water. The resultant mixture was stirred for about five minutes and concentrated under reduced pressure. To the residue was added a mixture of chloroform and methanol. The mixture was stirred under heating. Insoluble materials were removed by filtration and then the filtrate was concentrated under reduced pressure to give crude crystals, to which was added a mixture of chloroform and methanol (4:1). The mixture was stirred under heating to give crystals, which were separated by filtration to give crystalline 4-amino-6-methanesulfonamidoquinazoline (1.45 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe reaction mixture was stirred for an hour under ice-
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added
  6. additiona mixture of chloroform and methanol
  7. stirringThe mixture was stirred
  8. temperatureunder heating
  9. customInsoluble materials were removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customto give crude crystals
  12. additionto which was added
  13. stirringThe mixture was stirred
  14. temperatureunder heating
  15. customto give crystals, which
  16. customwere separated by filtration

Sources & evidence

ORD record
ord-94a0b80abdc4485a9635eefe6ac4424f
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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