Ammonia → 4-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-ol

HRID 403664Notes

Reaction equation

HRID 403664 reaction equation
Cl.C([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[CH:11][N:10]=[C:9]2[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[CH:26])[CH:20]=1)(=O)C.N>CO>[C:25]([C:21]1[CH:20]=[C:19]([NH:18][C:9]2[C:8]3[C:13](=[CH:14][C:15]([O:16][CH3:17])=[C:6]([OH:5])[CH:7]=3)[N:12]=[CH:11][N:10]=2)[CH:24]=[CH:23][CH:22]=1)#[CH:26]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86659918HCID 86659918, compound

Product 1

HCID 219252124-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-olYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yl acetate hydrochloride (10 g, 0.027 mol), methanol (250 ml) and 25% aqueous ammonia (8 ml, 0.106 mol, 3.93 equiv) was stirred at room temperature for 17 hours and then heated to reflux for 1.5 hours. The mixture was cooled and the precipitate was formed and isolated and dried to give 5.66 g product. MS (ESI) m/z: 307 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. customthe precipitate was formed
  5. customisolated
  6. customdried

Sources & evidence

ORD record
ord-2c03765ed6134140a1c048dfeb4a9b7d
Source dataset
uspto-grants-2014_06
Patent number
US08748453B2

Reaction notes

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