Hydrochloric Acid → 2-Chloro-N-(pyridin-4-yl)quinazolin-4-amine

HRID 1436237Notes

Reaction equation

HRID 1436237 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.Cl>C(O)(C)C>[Cl:1][C:2]1[N:11]=[C:10]([NH:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 17274-AminopyridineHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 226932532-Chloro-N-(pyridin-4-yl)quinazolin-4-amineYield 61.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred suspension of 2,4-dichloroquinazoline (42 mg, 0.21 mmol) and 4-aminopyridine (21 mg, 0.22 mmol) in 3 mL of anhydrous isopropanol was added a drop of concentrated HCl and the mixture was stirred overnight. Solid precipitates were observed and the mixture was filtered. The solid was washed with cold isopropanol and dried to give the title compound as white solid (38 mg, 0.13 mmol, 61%). 1H NMR (DMSO-d6): 8.60 (d, J=7.5 Hz, 2H), 8.18-8.20 (m, 2H), 8.07-8.10 (m, 1H), 7.90-7.96 (m, 1H), 7.18 (d, J=7.8 Hz, 2H).

Workup

  1. customSolid precipitates
  2. filtrationthe mixture was filtered
  3. washThe solid was washed with cold isopropanol
  4. customdried

Sources & evidence

ORD record
ord-7ea2936be0e74cc08e7cfb99e4fc2ba9
Source dataset
uspto-grants-2009_11
Patent number
US07618975B2

Reaction notes

Loading…