Diethyl (ethoxymethylene)malonate → 2-[5-{2,2-Bis(ethoxycarbonyl)-vinylamino}-2-propoxyphenyl]-8-azapurin-6-one

HRID 1863127Notes

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[CH:25]=[C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])C>S1(CCCC1)(=O)=O>[CH4:2].[CH2:35]([O:34][C:32]([C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][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:33])[CH3:36]

Participants

Conditions

Temperature: 140 °C

Procedure

A suspension of 2-(5-amino-2-propoxyphenyl)-8-azapurin-6-one (1.43 g) in dry sulpholane (15 ml) was treated with diethyl ethoxymethylenemalonate (1.25 g). The mixture was then stirred at 140° C. for one hour, under a slight vacuum in order to remove ethanol. After cooling, the mixture was poured with stirring into dilute hydrochloric acid (150 ml; 2 N), to give a buff-coloured gum which, on scratching, crystallised. Recrystallisation twice from a mixture of dimethylformamide and water, with the aid of charcoal, gave 2-[5-{2,2-bis(ethoxycarbonyl)-vinylamino}-2-propoxyphenyl]-8-azapurin-6-one (1.3 g), m.p. 226°-227° C.

Workup

customto remove ethanol
temperatureAfter cooling
additionthe mixture was poured
stirringwith stirring into dilute hydrochloric acid (150 ml; 2 N)
customto give a buff-coloured gum which
customcrystallised
customRecrystallisation
additiontwice from a mixture of dimethylformamide and water

Sources & evidence

ORD record: ord-b4180c32dcaa46289c9a2b6c5a30b287
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167568

Reaction notes

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