Dimethyl acetylenedicarboxylate → (Z)-2-[5-{1,2-bis(methoxycarbonyl)vinylamino}-2-propoxyphenyl]-8-azapurin-6-one

HRID 1863128Notes

Reaction equation

HRID 1863128 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][CH2:20][CH3:21])=[C:6]([C:8]2[N:16]=[C:15]3[C:11](=[N:12][N:13]=[N:14]3)[C:10](=[O:17])[N:9]=2)[CH:7]=1.[C:22]([C:28]([O:30][CH3:31])=[O:29])#[C:23][C:24]([O:26][CH3:27])=[O:25]>CO>[CH3:27][O:26][C:24](/[C:23](/[NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][CH2:20][CH3:21])=[C:6]([C:8]2[N:16]=[C:15]3[C:11](=[N:12][N:13]=[N:14]3)[C:10](=[O:17])[N:9]=2)[CH:7]=1)=[CH:22]/[C:28]([O:30][CH3:31])=[O:29])=[O:25]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 203929612-(5-Amino-2-propoxyphenyl)-8-azapurin-6-one

Product 1

HCID 70601716(Z)-2-[5-{1,2-bis(methoxycarbonyl)vinylamino}-2-propoxyphenyl]-8-azapurin-6-oneYield 46.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(5-Amino-2-propoxyphenyl)-8-azapurin-6-one (1.43 g), dimethyl acetylenedicarboxylate (0.85 g) and dry methanol (20 ml) were stirred and heated together at reflux for 5 hours. The resulting mixture was then cooled in an ice-bath for 30 minutes and the resulting yellow crystalline precipitate was filtered off and recrystallised from ethanol to give (Z)-2-[5-{1,2-bis(methoxycarbonyl)vinylamino}-2-propoxyphenyl]-8-azapurin-6-one (1.0 g), m.p. 199°-200° C. (with decomposition).

Workup

  1. temperatureheated together
  2. temperatureat reflux for 5 hours
  3. temperatureThe resulting mixture was then cooled in an ice-bath for 30 minutes
  4. filtrationthe resulting yellow crystalline precipitate was filtered off
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-0a37eddbe9c24cbabd672e8185dbbcaf
Source dataset
uspto-grants-1979_09
Patent number
US04167568

Reaction notes

Loading…