Adenine → HCID 20207437, compound

HRID 542890Notes

Reaction equation

HRID 542890 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(N(CC)CC)C.C(O[CH:21]=[C:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>CN(C)C=O>[N:10]1[C:2]([NH:1][CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:3]2[C:7]([N:6]=[CH:5][NH:4]2)=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 190AdenineHCID 6871Diethyl (ethoxymethylene)malonateHCID 8471Triethylamine

Product 1

HCID 20207437HCID 20207437, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-aminopurine (13.5 g), triethylamine (10.1 g) and 2-ethoxy-1,1-bis(ethoxycarbonyl)ethene (21.6 g) in dimethylformamide (100 ml) was heated at reflux for 16 hours. It was then cooled and the product which separated was crystallised from dimethylformamide and washed with diethyl ether, to give 2-(purin-6-ylamino)-1,1-bis(ethoxycarbonyl)ethene (23 g), in the form of colourless, fluffy crystals, m.p. 234° C. (with decomposition).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. temperatureIt was then cooled
  4. customthe product which separated
  5. customwas crystallised from dimethylformamide
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b35e3422fa2c443e80d0759459a0433c
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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