Ammonium fluoride → HCID 59242085, compound

HRID 1876156Notes

Reaction equation

HRID 1876156 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH4+].[F-]>C(O)(C)C>[CH:17]([O:20][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)([CH3:18])[CH3:16]

Participants

4

Reactant 2

HCID 25516Ammonium fluorideHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 59242085HCID 59242085, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (2-chloroquinazolin-4-yl)-(4-methoxyphenyl)-methylamine 0.150 g (0.5 mmol) with NH4F 0.500 g (13.5 mmol) in isopropanol 4 mL was stirred at reflux for 14 h. After removal of isopropanol, the residue was dissolved in dichloromethane, and the organic solution was washed with water, and dried over anhydrous MgSO4. After removal of solvent under reduced pressure, the title compound was obtained. 1H NMR (CD3OD, 400 MHz) δ 7.57-7.60 (m, 1H), 7.42-7.46 (m, 1H), 7.10-7.18 (m, 2H), 6.89-6.97 (m, 3H), 6.79-6.84 (m, 1H), 5.45-5.51 (m, 1H), 3.83 (s, 3H), 3.58 (s, 3H), 1.46 (d, J=6.3 Hz, 6H); HRMS (ES) m/z calcd for C19H21N3O2 (M+H) 324.1706, found 324.1954.

Workup

  1. temperatureat reflux for 14 h
  2. customAfter removal of isopropanol
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washthe organic solution was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customAfter removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-ba951fb0a5c64224aea1628450ac3701
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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