Potassium Carbonate → 6-Methoxy-7-(3-morpholinopropoxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one

HRID 1357718Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (4.51 g) was added to 7-hydroxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin4-one (2.0 g) in dimethylformamide (50 ml) followed by 3-morpholinopropyl chloride (1.3 g) and the reaction was stirred at 100° C. for 6 hours. After cooling the solid was removed by filtration and the filtrate was evaporated and was purified by eluting through a silica column with 10% methanol in methylene chloride to yield 6-methoxy-7-(3-morpholinopropoxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one as a solid (1.85 g, 65%); NMR: 1.1 (s, 9H), 1.9 (m, 2H), 2.4 (broad m, 6H), 3.55 (m, 4H), 3.88 (s, 3H), 4.16 (m, 2H), 5.89 (s, 2H), 7.13 (s, 1H), 7.47 (s, 1H), 8.32 (s, 1H); m/s: M+H+ 434.

Workup

temperatureAfter cooling the solid
customwas removed by filtration
customthe filtrate was evaporated
customwas purified
washby eluting through a silica column with 10% methanol in methylene chloride

Sources & evidence

ORD record: ord-de7e0445e127417c89b8cb183e10c5f8
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06593333B1

Reaction notes

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