Sodium Hydroxide → 5,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one

HRID 591603Notes

Reaction equation

HRID 591603 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[NH:25][C:24](=[O:26])[C:23]4[C:18](=[CH:19][C:20]([O:29][CH3:30])=[CH:21][C:22]=4[O:27][CH3:28])[N:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>Cl>[CH3:28][O:27][C:22]1[CH:21]=[C:20]([O:29][CH3:30])[CH:19]=[C:18]2[C:23]=1[C:24](=[O:26])[NH:25][C:16]([C:13]1[CH:14]=[CH:15][C:10]([N:7]3[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]3)=[CH:11][CH:12]=1)=[N:17]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1359390892-(4-(4-acetylpiperazin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one

Product 1

HCID 1359390885,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-oneYield 66%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-(4-(4-acetylpiperazin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one (1.93 g, 4.7 mmol) and 2 M HCl (200 mL) was heated at reflux for 9 hours. Then, the mixture was cooled to room temperature, basified to pH 8 with 2 N NaOH, extracted with CH2Cl2 (3×300 mL), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with 92:7:1 to 6:3:1 CHCl3/MeOH/concentrated NH4OH, to afford the title compound (1.13 g, 66%). 1H NMR (300 MHz, DMSO-d6): δ 8.08 (d, J=8.9 Hz, 2H), 6.99 (d, J=8.9 Hz, 2H), 6.68 (d, J=2.3 Hz, 1H), 6.47 (d, J=2.3 Hz, 1H), 3.88 (s, 3H), 3.83 (s, 3H), 3.19-3.23 (m, 4H), 2.81-2.84 (m, 4H); APCI MS m/z 367 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 9 hours
  3. extractionextracted with CH2Cl2 (3×300 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 92:7:1 to 6:3:1 CHCl3/MeOH/concentrated NH4OH

Sources & evidence

ORD record
ord-c7124abd0f074cfa8b79ebab6aed5997
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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