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

HRID 454238Notes

Reaction equation

HRID 454238 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-fbdd7638d0f6465d8bbe59ea90241b24
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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