6-Chloropurine riboside → N-[2-(2,5-dihydro-1H-pyrrol-1-yl) ethyl]adenosine, monohydrochloride

HRID 345167Notes

Reaction equation

HRID 345167 reaction equation
[CH:1]1[N:6]=[C:5]([Cl:7])[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.[N:20]1([CH2:25][CH2:26][NH2:27])[CH2:24][CH:23]=[CH:22][CH2:21]1>C(O)C>[ClH:7].[N:20]1([CH2:25][CH2:26][NH:27][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])[CH2:24][CH:23]=[CH:22][CH2:21]1

Participants

4

Reactant 2

HCID 930036-Chloropurine ribosideHCID 129736562-(2,5-dihydro-1H-pyrrol-1-yl)ethan-1-amine

Product 1

HCID 131717027N-[2-(2,5-dihydro-1H-pyrrol-1-yl) ethyl]adenosine, monohydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6 chloropurine riboside (1.27 g, 4.42 mmol) in 10 ml of absolute ethanol was added 2-(2,5-dihydro-1H-pyrrol-1-yl)-1-ethanamine (prepared in accordance with Arzneim. Forsch. 21 (12) 2089 (1971)) in an amount of 0.54 g (4.9 mmol). The reaction mixture was heated under reflux for 40 hours. Concentration of the reaction mixture in vacuo gave a residue which was chromatographed on cellulose powder (Whatman CC 31). The eluent was 85 parts n-butanol and 15 parts water. Fraction monitoring was accomplished by thin layer chromatography on silica gel (Kieselgel 60 F254) eluting with a mixture of 20 parts methanol, 79 parts methylene chloride and one part ammonium hydroxide. The chromatography gave a glass which was azeotroped with water 3 times to remove the n butanol. Lyophilization of the aqueous solution gave the title compound in an amount of 0.41 g (21g yield) as a white powder (mp 88°-105° C.)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 40 hours
  3. customConcentration of the reaction mixture in vacuo gave a residue which
  4. customwas chromatographed on cellulose powder (Whatman CC 31)
  5. washeluting with a mixture of 20 parts methanol, 79 parts methylene chloride and one part ammonium hydroxide
  6. customThe chromatography gave a glass which
  7. customwas azeotroped with water 3 times
  8. customto remove the n butanol

Sources & evidence

ORD record
ord-9bfaf0fae7e84279aa4cb65aa267073f
Source dataset
uspto-grants-1991_10
Patent number
US05055569

Reaction notes

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