Ethyl orthoformate → 7-Methoxy-6-benzyloxyquinazolone

HRID 1010802Notes

Reaction equation

HRID 1010802 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][C:3]=1[C:4]([NH2:6])=O.[CH2:21]([O:23]C(OCC)OCC)C>>[CH3:12][O:11][C:9]1[CH:10]=[C:2]2[C:3]([CH:4]=[N:6][C:21](=[O:23])[NH:1]2)=[CH:7][C:8]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 593619042-Amino-5-(benzyloxy)-4-methoxybenzamide

Product 1

HCID 671387577-Methoxy-6-benzyloxyquinazolone

Procedure

2-Amino-4-methoxy-5-benzyloxybenzamide (JMC, 20, 146) (5 g) was mixed with triethylorthoformate (15 ml) and refluxed overnight. The reaction solution was cooled and triturated with EtOAc (40 ml) then filtered to give 7-methoxy-6-benzyloxyquinazolone (3.2 g). This product was mixed with DIPEA (15 ml) and to the solution was added POCl3 (3 ml) slowly. The reaction mixture was refluxed for 30 minutes and cooled, then poured into a stirred mixture of ice and CHCl3. The solution was further extracted with CHCl3 three times and washed with H2O followed by brine, dried over Na2SO4 and evaporated to give a light brown solid as the chloride for next step without further purification.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction solution was cooled
  3. customtriturated with EtOAc (40 ml)
  4. filtrationthen filtered

Sources & evidence

ORD record
ord-fbbf9a4ebf864caf9a2f212d3176c0c9
Source dataset
uspto-grants-2011_07
Patent number
US07977346B2

Reaction notes

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