Trimethyl orthoformate → HCID 136054910, compound

HRID 1885858Notes

Reaction equation

HRID 1885858 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[NH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH2:19][CH2:20][CH3:21])=[N:9]2)=[CH:4][CH:3]=1.[CH3:23]OC(OC)OC>>[CH3:23][NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[NH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH2:19][CH2:20][CH3:21])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 136210639HCID 136210639, compound

Product 1

HCID 136054910HCID 136054910, compound

Procedure

7-amino-2-(2-propoxyphenyl)-4(3H)-quinazolinone (0.5 g) was heated under reflux in trimethylorthoformate (5 ml) for 22 hours. The reaction mixture was evaporated to dryness, the residue dissolved in dry tetrahydrofuran and treated with sodium borohydride (0.3 g) and 4A molecular sieves for 24 hours. The reaction mixture was partitioned between water and dichloromethane, the organic layer separated, dried (magnesium sulphate) and evaporated. The residue was recrystallised from dichloromethane-diethyl ether to give 7-methylamino-2-(2-propoxyphenyl)-4(3H)-quinazolinone 0.17 g, m.p. 204°-205° C.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in dry tetrahydrofuran
  3. additiontreated with sodium borohydride (0.3 g) and 4A molecular sieves for 24 hours
  4. customThe reaction mixture was partitioned between water and dichloromethane
  5. customthe organic layer separated
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated
  8. customThe residue was recrystallised from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-9013732ea214444d87f94c59b672e977
Source dataset
uspto-grants-1992_09
Patent number
US05147875

Reaction notes

Loading…