Water → 3-benzyl-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one

HRID 455912Notes

Reaction equation

[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([O:20][CH3:21])=[C:14]([OH:19])[CH:15]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH:33]1[CH2:42][CH2:41][C:36]2([O:40][CH2:39][CH2:38][O:37]2)[CH2:35][CH2:34]1)(=O)=O.O>CN(C)C=O>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([O:20][CH3:21])=[C:14]([O:19][CH:33]3[CH2:42][CH2:41][C:36]4([O:40][CH2:39][CH2:38][O:37]4)[CH2:35][CH2:34]3)[CH:15]=2)[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

20.00 g 3-benzyl-6-hydroxy-7-methoxy-3H-quinazolin-4-one in 150 ml N,N-dimethylformamide are heated to 50° C., then 16.00 g potassium carbonate and 20.00 g 1,4-dioxa-spiro[4.5]dec-8-yl methanesulphonate are added and the reaction mixture is stirred overnight at 80° C. Then another 6.00 g potassium carbonate and 8.00 g 1,4-dioxa-spiro[4.5]dec-8-yl methanesulphonate are added and the mixture is stirred for a further 4 h at 80° C. Within the next 24 h a total of a further 6.00 g potassium carbonate and 10.00 g 1,4-dioxa-spiro[4.5]dec-8-yl methanesulphonate are added batchwise until the reaction is complete. After cooling to ambient temperature a total of 450 ml of water are very slowly added dropwise with stirring, whereupon a precipitate is formed which is suction filtered, washed with water and dried.

Workup

stirringthe mixture is stirred for a further 4 h at 80° C
additionare very slowly added dropwise
stirringwith stirring, whereupon a precipitate
customis formed which
filtrationfiltered
washwashed with water
customdried

Sources & evidence

ORD record: ord-692baae098484a1f87a696d275eb0314
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497369B2

Reaction notes

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