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Ethanol → (RS)-S-[3-({[4-(Isopropylamino)-6-methoxyquinazolin-7-yl]oxy}methyl)phenyl]-S-methylsulphoximide

HRID 249974
Notes
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Reaction equation

HRID 249974 reaction equation
C(OC([N:6]=[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][C:18]2[CH:27]=[C:26]3[C:21]([C:22]([NH:28][CH:29]([CH3:31])[CH3:30])=[N:23][CH:24]=[N:25]3)=[CH:20][C:19]=2[O:32][CH3:33])[CH:11]=1)([CH3:9])=[O:8])=O)C.C(O)C.[O-]CC.[Na+]>ClCCl.CO>[CH:29]([NH:28][C:22]1[C:21]2[C:26](=[CH:27][C:18]([O:17][CH2:16][C:12]3[CH:11]=[C:10]([S:7]([CH3:9])(=[NH:6])=[O:8])[CH:15]=[CH:14][CH:13]=3)=[C:19]([O:32][CH3:33])[CH:20]=2)[N:25]=[CH:24][N:23]=1)([CH3:30])[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 57787986(RS)-N-(Ethoxycarbonyl)-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}-methyl)phenyl]-S-methylsulphoximide

Product 1

HCID 57788004(RS)-S-[3-({[4-(Isopropylamino)-6-methoxyquinazolin-7-yl]oxy}methyl)phenyl]-S-methylsulphoximideYield 36%

Reagents, catalysts & solvents 1

HCID 21226129
Dichloromethane methanol
Solvent

Conditions

Temperature
80 °C

Procedure

(RS)-N-(Ethoxycarbonyl)-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}-methyl)phenyl]-S-methylsulphoximide (105 mg, 0.22 mmol) is introduced into 2.5 ml of ethanol. 1.0 ml of a 1-molar ethanolic sodium ethoxide solution is added and the mixture is heated to 80° C., until starting material is no longer present according to TLC checking (eluent dichloromethane/methanol 10:1). The reaction solution is concentrated in vacuo, and the residue is taken up in ethyl acetate and washed with saturated sodium carbonate solution. The organic phase is dried over sodium sulphate and concentrated. The crude product is purified by preparative HPLC and the desired product is obtained in 36% yield (32 mg).

Workup

  1. concentrationThe reaction solution is concentrated in vacuo
  2. washwashed with saturated sodium carbonate solution
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-63ea4ec651fd49ed9c78ba2da63f3ba8
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863283B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes