Acetic Anhydride → HCID 178488518, compound

HRID 1774111Notes

Reaction equation

HRID 1774111 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[CH:8]=2)[N:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([NH:1][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[CH:8]=2)[N:3]=1)(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 178488519HCID 178488519, compound

Product 1

HCID 178488518HCID 178488518, compoundYield 90%

Procedure

A suspension of the crude 2-amino-6-(3,4-dimethoxyphenyl)-4-hydroxyquinazoline from example 5 (3.0 g, 10 mmol) in acetic anhydride (20 ml) was refluxed for 40 minutes. After concentration under reduced pressure, the residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1:40), yielding the title compound as a white solid (3.05 g, yield: 90%) which was characterized by its mass spectrum as follows: MS (m/z): 340 ([M+H]+, 100).

Workup

  1. temperaturewas refluxed for 40 minutes
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography
  4. additiona mixture of methanol and dichloromethane (in a ratio of 1:40),

Sources & evidence

ORD record
ord-952cabc39b834fcc931d4ec6715039c3
Source dataset
uspto-grants-2016_02
Patent number
US09259426B2

Reaction notes

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