Sodium Hydroxide → 2-(5-Amino-2-ethoxyphenyl)-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-one

HRID 232563Notes

Reaction equation

HRID 232563 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[C:13]1[NH:14][C:15](=[O:26])[C:16]2[N:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:17]=2[N:18]=1)[CH3:2].[OH-].[Na+]>C(O)C>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:13]2[NH:14][C:15](=[O:26])[C:16]3[N:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:17]=3[N:18]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1354943292-(2-Ethoxy-5-nitrophenyl)-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 1354445822-(5-Amino-2-ethoxyphenyl)-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-oneYield 71.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride dihydrate (2.48 g, 0.011 mol) was added to a stirred solution of 2-(2-ethoxy-5-nitro-phenyl)-8-n-propylprido [3,2-d]pyrimidin-4(3H)-one (Example 10; 0.78 g, 0.0022 mol) in ethanol (10 ml) and the mixture was heated under reflux for 2 hours, allowed to cool, basified to pH 11 by the addition of 10% aqueous sodium hydroxide solution, and then extracted with methanol:dichloromethane (1:9, 3×50 ml). The organic extracts were combined, dried (MgSO4) and evaporated under vacuum, then the residue was chromatographed on silica gel (12 g) using a methanol in dichloromethane elution gradient (0-2% methanol). Trituration of the product with hexane:ethyl acetate gave the title compound as a colourless solid (0.51 g, 71%), m.p. 156°-158° C. Found: C,66.61; H,6.20; N,17.14. C18H20N4O2 requires C,66.65; H,6.22; N,17.27%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. extractionextracted with methanol:dichloromethane (1:9, 3×50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under vacuum
  7. customthe residue was chromatographed on silica gel (12 g)
  8. washa methanol in dichloromethane elution gradient (0-2% methanol)

Sources & evidence

ORD record
ord-556d26ff5a0640a281665c6f6d3691af
Source dataset
uspto-grants-1997_01
Patent number
US05591742

Reaction notes

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