Acetic Anhydride → HCID 178488518, compound

HRID 1187257Notes

Reaction equation

HRID 1187257 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 crude 2-amino-6-(3,4-dimethoxyphenyl)-4-hydroxy-quinazoline (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-d2836ac407814402aa86d533b51012dc
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

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