Ammonia → 6-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one

HRID 1791760Notes

Reaction equation

HRID 1791760 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:30])[N:17](COC(=O)C(C)(C)C)[CH:18]=[N:19]3)=[CH:14][C:13]=2[O:31][CH3:32])[CH2:4][CH2:3]1.N>CO>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:30])[NH:17][CH:18]=[N:19]3)=[CH:14][C:13]=2[O:31][CH3:32])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 220306066-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 1354581696-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-oneYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 7-(3-(4-methylpiperazin-1-yl)propoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (31.8 g, 71.3 mmol) in methanol saturated with ammonia was stirred at ambient temperature overnight. The volatiles were removed under vacuum. The solid was triturated with ether containing about 10% of methylene chloride, filtered, washed with ether containing about 10% methylene chloride and dried under vacuum to give 7-(3-(4-methylpiperazin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (22.63 g, 95%).

Workup

  1. customThe volatiles were removed under vacuum
  2. customThe solid was triturated with ether containing about 10% of methylene chloride
  3. filtrationfiltered
  4. washwashed with ether containing about 10% methylene chloride
  5. customdried under vacuum

Sources & evidence

ORD record
ord-93c9f371cee641829e25238921c4f162
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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