Water → 3-benzyl-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one
Reaction equation
C(=O)([O-])[O-].[K+].[K+].CS([O:11][CH:12]1[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:14][CH2:13]1)(=O)=O.[CH2:22]([N:29]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][C:34]([O:41][CH3:42])=[C:35](O)[CH:36]=2)[N:31]=[CH:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O>[CH2:22]([N:29]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][C:34]([O:41][CH3:42])=[C:35]([O:11][CH:12]3[CH2:21][CH2:20][C:15]4([O:19][CH2:18][CH2:17][O:16]4)[CH2:14][CH2:13]3)[CH:36]=2)[N:31]=[CH:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
16.0 g potassium carbonate and 20.0 g 8-methanesulphonyloxy-1,4-dioxa-spiro[4.5]decan are added at 50° C. to 20.0 g 3-benzyl-3,4-dihydro-4-oxo-6-hydroxy-7-methoxy-quinazoline in 150 ml N,N-dimethylformamide and the mixture is vigorously stirred for 18 hours at 80° C. To complete the reaction potassium carbonate and 8-methanesulphonyloxy-1,4-dioxa-spiro[4.5]decan are each added three times and in each case the mixture is stirred for several hours at 80° C. The reaction mixture is cooled and slowly combined with a total of 500 ml of water. The precipitate is suction filtered, washed with water and dried.
Workup
- additioneach added three times
- stirringin each case the mixture is stirred for several hours at 80° C
- temperatureThe reaction mixture is cooled
- filtrationfiltered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-f661c0a74a9c41aea1d7d3d666c0fe8f
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372855B2
Reaction notes
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