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

HRID 1876076Notes

Reaction equation

HRID 1876076 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-ebebb0afe9794a42a1d5ea25562173c4
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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