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4-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol → 6-{[3-chloro-5-(2-methoxyethoxy)pyridin-2-yl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)quinazoline-4-amine

HRID 1517302
Notes
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Reaction equation

HRID 1517302 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[CH3:20][N:21]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([OH:37])[CH:35]=3)[N:30]=[CH:29][N:28]=2)=[N:22]1.O.[Cl-].[Na+]>C(Cl)(Cl)Cl.CN(C)C(=O)C>[Cl:8][C:7]1[C:2]([O:37][C:34]2[CH:35]=[C:36]3[C:31](=[CH:32][CH:33]=2)[N:30]=[CH:29][N:28]=[C:27]3[NH:26][C:23]2[CH:24]=[CH:25][N:21]([CH3:20])[N:22]=2)=[N:3][CH:4]=[C:5]([O:9][CH2:10][CH2:11][O:12][CH3:13])[CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 231603824-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-olHCID 23665647Potassium tert-butoxideHCID 57417360Sodium chloride; waterHCID 866459022,3-Dichloro-5-(2-methoxyethoxy)pyridine

Product 1

HCID 595088886-{[3-chloro-5-(2-methoxyethoxy)pyridin-2-yl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)quinazoline-4-amineYield 28.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
180 °C

Procedure

2,3-Dichloro-5-(2-methoxyethoxy)pyridine (127 mg, 0.57 mmol) and potassium tert-butoxide (70 mg, 0.62 mmol) were added to an N,N-dimethylacetamide solution (2 ml) of 4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol (60 mg, 0.25 mmol), and stirred overnight at 180° C. under a nitrogen atmosphere in a sealed tube. The reaction solution was cooled with ice, then sodium chloride water and chloroform were added, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by reversed-phase liquid chromatography (YMC CombiPrep Pro C18 AS-360-CC) to obtain the entitled compound (30 mg, yield: 28%) as a pale orange amorphous solid.

Workup

  1. temperatureThe reaction solution was cooled with ice
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by reversed-phase liquid chromatography (YMC CombiPrep Pro C18 AS-360-CC)

Sources & evidence

ORD record
ord-358d157985ed42a99633ba4f3ae65b7d
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08232284B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes