6-Methoxy-7-(3-morpholinopropoxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one → 6-methoxy-7-(3-morpholin-4-ylpropoxy)-1H-quinazolin-4-one

HRID 634754Notes

Reaction equation

HRID 634754 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][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:9]=[CH:8][N:7](COC(=O)C(C)(C)C)[C:6]2=[O:31]>N>[OH:31][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 1

HCID 227322766-Methoxy-7-(3-morpholinopropoxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 1784867726-methoxy-7-(3-morpholin-4-ylpropoxy)-1H-quinazolin-4-oneYield 79%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 3,4-dihydro-6-methoxy-3-((pivaloyloxy)methyl)-7-(3-morpholinopropoxy)quinazolin-4-one (4.93 g, 11.4 mmol) in a saturated solution of methanolic ammonia (70 ml) was stirred at ambient temperature for 2 days. The volatiles were removed by evaporation. The solid residue was suspended in ether, collected by filtration, washed with ether and dried under vacuum to give 4-hydroxy-6-methoxy-7-(3-morpholinopropoxy)quinazoline (2.87 g, 79%).

Workup

  1. customThe volatiles were removed by evaporation
  2. filtrationcollected by filtration
  3. washwashed with ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e5917fa89c2042daa9bfd94394292ca9
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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