Triethylamine → N6-[1H-inden-3-yl]methyl adenosine

HRID 414174Notes

Reaction equation

HRID 414174 reaction equation
[CH:1]1[N:6]=[C:5](Cl)[C:4]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[C:3]=2[N:2]=1.[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][NH2:30])=[CH:21]1.C(N(CC)CC)C>C(O)C>[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][NH:30][C:5]2[C:4]3[N:8]=[CH:9][N:10]([C:3]=3[N:2]=[CH:1][N:6]=2)[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]2[OH:19])=[CH:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 10931565[1H-inden-3-yl]methylamine

Product 1

HCID 14348698N6-[1H-inden-3-yl]methyl adenosineYield 22.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction mixture of 1.4 g of 6-chloropurine riboside, 1.6 g of [1H-inden-3-yl]methylamine as prepared in Example E hereinafter and 1.5 g of triethylamine in 150 ml ethanol is refluxed for 24 hours. Volatiles are evaporated under reduced pressure and residue is purified on Prep-500A using one prepacked silica gel column and 10% methanoldichloromethane as an eluant at a rate of 150 ml/min. Evaporation of solvent from pure fractions affords 0.43 g (22%) of N6 -[1H-inden-3-yl]methyl adenosine having a melting point of 200°-202° C. Anals. calcd. for C20H21N5O4.0.3 CH3OH; Found: C=60.20; H=5.53; N=17.29; C=60.49; H=5.44; N=17.25.

Workup

  1. temperatureis refluxed for 24 hours
  2. customVolatiles are evaporated under reduced pressure and residue
  3. customis purified on Prep-500A using one prepacked silica gel column and 10% methanoldichloromethane as an eluant at a rate of 150 ml/min
  4. customEvaporation of solvent from pure fractions

Sources & evidence

ORD record
ord-add7245323be4f9e875ff40e2063eee6
Source dataset
uspto-grants-1988_12
Patent number
US04791103

Reaction notes

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