Sulfolane → 2-[5-(2-Ethoxycarbonylcyclopent-1-enylamino)-2-propoxyphenyl]-8-azapurin-6-one

HRID 1863135Notes

Reaction equation

HRID 1863135 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(O[C:25]1[CH2:29][CH2:28][CH2:27][C:26]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])C.S1(CCCC1)(=O)=O>Cl>[CH2:33]([O:32][C:30]([C:26]1[CH2:27][CH2:28][CH2:29][C:25]=1[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)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 12448915Ethyl 2-ethoxycyclopent-1-ene-1-carboxylateHCID 203929612-(5-Amino-2-propoxyphenyl)-8-azapurin-6-one

Product 1

HCID 203929822-[5-(2-Ethoxycarbonylcyclopent-1-enylamino)-2-propoxyphenyl]-8-azapurin-6-oneYield 28.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred mixture of 2-(5-amino-2-propoxyphenyl)-8-azapurin-6-one (2.02 g), ethyl 2-ethoxy-1-cyclopentenecarboxylate (1.43 g) and dry sulpholane (20 ml) was heated at 125°-130° C. for 2 hours. The solution was then cooled and poured into dilute hydrochloric acid (200 ml; 2 N) and the yellow solid obtained was filtered off and recrystallised from a mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate to give 2-[5-(2-ethoxycarbonylcyclopent-1-enylamino)-2-propoxyphenyl]-8-azapurin-6-one (0.85 g), m.p. 164°-165° C.

Workup

  1. temperaturewas heated at 125°-130° C. for 2 hours
  2. temperatureThe solution was then cooled
  3. customthe yellow solid obtained
  4. filtrationwas filtered off
  5. customrecrystallised from a mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate

Sources & evidence

ORD record
ord-afd73e13d2bc4c22b2e64f4b00bfdebb
Source dataset
uspto-grants-1979_09
Patent number
US04167568

Reaction notes

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