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

HRID 1672125Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[O:7]1[C:11]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.[CH2:17]([N:24]1[C:33](=[O:34])[C:32]2[C:27](=[CH:28][C:29]([O:36][CH3:37])=[C:30]([OH:35])[CH:31]=2)[N:26]=[CH:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:17]([N:24]1[C:33](=[O:34])[C:32]2[C:27](=[CH:28][C:29]([O:36][CH3:37])=[C:30]([O:35][CH:14]3[CH2:15][CH2:16][C:11]4([O:10][CH2:9][CH2:8][O:7]4)[CH2:12][CH2:13]3)[CH:31]=2)[N:26]=[CH:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

At 50° C. 16.0 g potassium carbonate and 20.0 g of 8-methanesulphonyloxy-(1,4-dioxa-spiro[4,5]decan are added 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]decane are each added three times more 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

customAt 50° C
additioneach added three times more
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-ca038b4d55554d0ca98298a48e3b550f
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998949B2

Reaction notes

Loading…