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Potassium Carbonate → 7-((2-Chloro-6-methoxy-4-pyridyl)methoxy)-6-methoxy4-phenoxyquinazoline

HRID 1420998
Notes
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Reaction equation

HRID 1420998 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:19][CH3:20].Cl.[Cl:22][C:23]1[CH:28]=[C:27]([CH2:29]Cl)[CH:26]=[C:25]([O:31][CH3:32])[N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:22][C:23]1[CH:28]=[C:27]([CH2:29][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:19][CH3:20])[CH:26]=[C:25]([O:31][CH3:32])[N:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 226250592-Chloro-4-(chloromethyl)-6-methoxypyridine hydrochlorideHCID 1354961377-Hydroxy-6-methoxy-4-phenoxyquinazoline

Product 1

HCID 226248857-((2-Chloro-6-methoxy-4-pyridyl)methoxy)-6-methoxy4-phenoxyquinazolineYield 83.5%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-hydroxy-6-methoxy-4-phenoxyquinazoline (1.1 g, 4.1 mmol), (prepared as described for the starting material in Example 13), 2-chloro-4-chloromethyl-6-methoxypyridine hydrochloride (0.88 g, 3.9 mmol) and potassium carbonate (2.0 g, 14 mmol) in DMF (20 ml) was heated at 80° C. for 1 hour. The mixture was allowed to cool, diluted with water and the precipitated product collected by filtration, washed with water and dried to give 7-((2-chloro-6-methoxy-4-pyridyl)methoxy)-6-methoxy4-phenoxyquinazoline (1.38 g, 79%).

Workup

  1. custom(prepared
  2. temperatureto cool
  3. filtrationthe precipitated product collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-852c14c3318648ca8750abebddaa06df
Source dataset
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06071921

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes