Sodium Hydroxide → HCID 57787952, compound

HRID 249989Notes

Reaction equation

HRID 249989 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([S:20][CH3:21])[CH:19]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:22][CH:23]([CH3:25])[CH3:24].ClC1C=CC=C(C(OO)=[O:34])C=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([S:20]([CH3:21])=[O:34])[CH:19]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:22][CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57788032HCID 57788032, compound

Product 1

HCID 57787952HCID 57787952, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

6-Bromo-N-isopropyl-7-{[5-(methylsulphanyl)pyridin-3-yl]methoxy}quinazolin-4-amine (430 mg, 1.03 mmol) is presented as an initial charge in 20 mL of chloroform and at 0° C. and at 0° C. admixed with meta-chloroperbenzoic acid (260 mg, 1.13 mmol). The batch is subsequently stirred at 0° C. for 45 minutes. The batch is introduced into 2N aqueous sodium hydroxide solution. The mixture is extracted with dichloro-methane, the organic phase is dried over sodium sulphate and the solvent is concentrated. Chromatography (silica gel, dichloromethane/methanol: 0→30% methanol) gives the desired product in 74% yield (330 mg).

Workup

  1. extractionThe mixture is extracted with dichloro-methane
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. concentrationthe solvent is concentrated

Sources & evidence

ORD record
ord-d3e3dc08523745ab8f8d351c4490b9ab
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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