Ammonia → 7-(2-(1-Methylpiperidin-4-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one

HRID 454229Notes

Reaction equation

HRID 454229 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:29])[N:16](COC(=O)C(C)(C)C)[CH:17]=[N:18]3)=[CH:13][C:12]=2[O:30][CH3:31])[CH2:4][CH2:3]1.N>CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:29])[NH:16][CH:17]=[N:18]3)=[CH:13][C:12]=2[O:30][CH3:31])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 111128387-(2-(1-Methylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 1354507917-(2-(1-Methylpiperidin-4-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-oneYield 101.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-(2-(1-methylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (4.2 g, 9.7 mmol) in methanol saturated with ammonia (150 ml) was stirred overnight at ambient temperature. The volatiles were removed under vacuum and the residue was triturated with ether. The solid was filtered, washed with ether and dried under vacuum to give 7-(2-(1-methylpiperidin-4-yl)ethoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (3.12 g, 100%).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue was triturated with ether
  3. filtrationThe solid was filtered
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-62367d55a4c8443d9dd6f4fb3ad701cb
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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