Sodium Bicarbonate → 7-(3-(1,1-Dioxothiomorpholino)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one
Reaction equation
ClC1C=CC([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][S:26](=[O:30])(=[O:29])[CH2:25][CH2:24]4)=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=C(F)C=1.C(=O)([O-])O.[Na+]>Cl.O>[O:30]=[S:26]1(=[O:29])[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][CH2:20][O:19][C:13]2[CH:12]=[C:11]3[C:16]([C:7](=[O:6])[NH:8][CH:9]=[N:10]3)=[CH:15][C:14]=2[O:17][CH3:18])[CH2:28][CH2:27]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 95 °C
Procedure
4-(4-Chloro-2-fluorophenoxy)-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazoline (3.5 g, 7 mmol) was dissolved in 2M aqueous hydrochloric acid (56 ml) and heated at 95° C. for 2 hours. The cooled reaction mixture was treated with solid sodium hydrogen carbonate solution to give a thick paste which was diluted with water and filtered. The solid was transferred to a flask and azeotroped with toluene twice to give a dry solid. The solid was flash chromatographed on silica eluting with dichloromethane and methanol (95/5). The relevant fractions were combined and evaporated to give 7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (2.26 g, 87%) as a white solid.
Workup
- customThe cooled reaction mixture
- customto give a thick paste which
- filtrationfiltered
- customThe solid was transferred to a flask
- customazeotroped with toluene twice
- customto give a dry solid
- customchromatographed on silica eluting with dichloromethane and methanol (95/5)
- customevaporated
Sources & evidence
- ORD record
- ord-6ae5ca74d9204b41a0e51d5e463bfa06
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492560B2
Reaction notes
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