Oxalic Acid → 5-Trifluoromethyl-quinazoline-2,4-diamine

HRID 655621Notes

Reaction equation

HRID 655621 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[C:9](O)(=[O:13])[C:10](O)=[O:11]>Cl>[NH:8]1[C:10](=[O:11])[C:9](=[O:13])[NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]1=2

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 59183,4-Diaminopyridine

Product 1

HCID 107970835-Trifluoromethyl-quinazoline-2,4-diamineYield 81.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 3,4-diaminopyridine (10 g, 0.068 mol) in 4N aqueous HCl (100 ml) is added oxalic acid (10.4 g, 0.082 mol) and the reaction mixture is refluxed for 20 h. The reaction mixture is cooled down and the solid precipitated is filtered, washed with water then dried under vacuum to afford 9 g (80%) of the title compound as a solid. HPLC (max plot) 98%. LC/MS: (ES+): 164.3.

Workup

  1. temperaturethe reaction mixture is refluxed for 20 h
  2. temperatureThe reaction mixture is cooled down
  3. customthe solid precipitated
  4. filtrationis filtered
  5. washwashed with water
  6. customthen dried under vacuum

Sources & evidence

ORD record
ord-60df395042a8448483e0880ae86baad2
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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