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

HRID 1791751Notes

Reaction equation

HRID 1791751 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-fdf85d2b5d344a6ab7a1ac655e9bb8a1
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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