3-Methoxyphenol → HCID 178418811, compound

HRID 7603

Reaction equation

HRID 7603 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.Cl[C:13]1[N:22]=[C:21]([NH:23][C:24]2[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][C:13]1[N:22]=[C:21]([NH:23][C:24]2[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

6

Reactant 4

HCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 219391632-Chloro-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine

Product 1

HCID 178418811HCID 178418811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (45 mg, 1.12 mmol) in THF (2 mL) is treated with 3-methoxyphenol (0.94 g, 7.6 mmol) and the reaction mixture is stirred until effervescence ceases. The THF is removed in vacuo and the above-prepared (2-chloroquinazolin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (150 mg, 0.51 mmol)) is added. The reaction mixture is stirred at 100° C. for 20 h, then poured into aqueous K2CO3 and stirred for 2 h at room temperature. The solid that forms is collected and re-crystallized from ethanol to give the product [2-(3-methoxyphenoxy)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.

Workup

  1. customThe THF is removed in vacuo
  2. stirringThe reaction mixture is stirred at 100° C. for 20 h
  3. stirringstirred for 2 h at room temperature
  4. customThe solid that forms is collected
  5. customre-crystallized from ethanol

Sources & evidence

ORD record
ord-d9d7db8763554a4e87f3deec5be27ca4
Source dataset
uspto-grants-2006_08
Patent number
US07087603B2

Linked notes

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