Cesium carbonate → (RS)-N-(Ethoxycarbonyl)-S-[3-({[4-(isopropylamino)-6-methoxyquinazolin-7-yl]oxy}-methyl)phenyl]-S-methylsulphoximide

HRID 249973Notes

Reaction equation

HRID 249973 reaction equation
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].Br[CH2:19][C:20]1[CH:21]=[C:22]([S:26]([CH3:34])(=[N:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:27])[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:32]([O:31][C:29]([N:28]=[S:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][O:17][C:11]2[CH:10]=[C:9]3[C:14]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][CH:7]=[N:8]3)=[CH:13][C:12]=2[O:15][CH3:16])[CH:21]=1)([CH3:34])=[O:27])=[O:30])[CH3:33]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 57788029(RS)-S-[3-(bromomethyl)phenyl]-N-(ethoxycarbonyl)-S-methylsulphoximideHCID 1358608004-(Isopropylamino)-6-methoxyquinazolin-7-ol

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(Isopropylamino)-6-methoxyquinazolin-7-ol (65 mg, 0.21 mmol) and (RS)-S-[3-(bromomethyl)phenyl]-N-(ethoxycarbonyl)-S-methylsulphoximide (102 mg, 0.27 mmol) are suspended in 14 ml of acetone. After addition of caesium carbonate (2427 mg, 0.74 mmol), the reaction mixture is stirred at reflux for 3 hours. After cooling, the batch is concentrated, the residue is taken up in ethyl acetate, and the organic phase is washed with water and dried over sodium sulphate. After removal of the solvent, the residue (144 mg, 97% of theory) is employed in the next reaction without further purification.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling
  3. concentrationthe batch is concentrated
  4. washthe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. customAfter removal of the solvent
  7. customthe residue (144 mg, 97% of theory) is employed in the next reaction without further purification

Sources & evidence

ORD record
ord-45546735ad3c4b4490aea5f859f67e4b
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

Loading…