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

HRID 1386308Notes

Reaction equation

HRID 1386308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[N:9]=[CH:8][N:7](COC(=O)C(C)(C)C)[C:6]2=[O:29].N>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[N:9]=[CH:8][NH:7][C:6]2=[O:29]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 217172866-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 1354756166-Methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-oneYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-methoxy-3-((pivaloyloxy)methyl)-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (524 mg, 1.3 mmol) in methanol saturated with ammonia (10 ml) was stirred for 20 hours at ambient temperature. The volatiles were removed by evaporation and the solid residue was triturated with ether, collected by filtration and dried under vacuum to give 6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (230 mg, 61%).

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe solid residue was triturated with ether
  3. filtrationcollected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-692385f746c646669481fd8e35892ce6
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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