Thionyl Chloride → 4-chloro-6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)quinazoline hydrochloride

HRID 279659Notes

Reaction equation

HRID 279659 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]([CH3:24])[C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19][N:18]=1)[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:28])=O>CN(C=O)C.C1(C)C=CC=CC=1>[ClH:28].[Cl:28][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:16]([CH3:24])[C:17]3[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19][N:18]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 1356711766-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 226249054-chloro-6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)quinazoline hydrochlorideYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3,4-dihydroquinazolin-4-one (250 mg, 0.73 mmol) in thionyl chloride (5 ml) and DMF (0.1 ml) was heated at reflux for 1 hour. The mixture was diluted with toluene and the volatiles were removed by evaporation. The residue was triturated with methylene chloride/ether, the solid was collected by filtration and dried under vacuum to give 4-chloro-6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)quinazoline hydrochloride (260 mg, 90%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customthe volatiles were removed by evaporation
  4. customThe residue was triturated with methylene chloride/ether
  5. filtrationthe solid was collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-16150b27b5a4447a9706f2a041ea241c
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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