Sodium Hydroxide → 3-((Pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 1791735Notes

Reaction equation

Cl.CO[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1OCC1CCNCC1)[N:10]=[CH:9][N:8]([CH2:22][O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:7]2=[O:30].[OH-].[Na+]>O>[C:24]([O:23][CH2:22][N:8]1[C:7](=[O:30])[C:6]2[C:11](=[CH:12][CH:13]=[CH:4][CH:5]=2)[N:10]=[CH:9]1)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 6-methoxy-7-(piperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one hydrochloride (34 g, 84 mmol), (prepared as described for the starting material in Example 12), in water cooled at 0° C. was added 1N sodium hydroxide until the mixture was at pH8. The solution was extracted with trichloromethane and the organic layer was dried (MgSO4), filtered and evaporated to give 6-methoxy-7-piperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (29 g).

Workup

custom(prepared
extractionThe solution was extracted with trichloromethane
dry with materialthe organic layer was dried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-1fedcee2041d4060b14263b35a021e3b
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074800B1

Reaction notes

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