Ethylamine → 2-Amino-9-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-6-ethylamino-9H-purine

HRID 465716Notes

Reaction equation

HRID 465716 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)=[C:4](Cl)[N:3]=1.[CH2:22]([NH2:24])[CH3:23]>C(#N)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)=[C:4]([NH:24][CH2:22][CH3:23])[N:3]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 476464((2S,3S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-3-azidotetrahydrofuran-2-yl)methanol

Product 1

HCID 211473252-Amino-9-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-6-ethylamino-9H-purineYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

2-Amino-9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6-chloro-9H-purine (0.23 g, 0.74 mmol) was dissolved in 20 mL anhydrous acetonitrile in a sealed tube. The solution was cooled to 0° C., saturated with ethylamine (Aldrich, lot #00115JV) and sealed. After heating at 70° C. for 16 hours, the reaction mixture was filtered and the filtrate evaporated to dryness. The residue was preloaded onto silica gel and eluted from a silica column using CHCl3 /MeOH (95:5, v/v). Combination and evaporation of appropriate fractions yielded 0.140 g (0.44 mmol, 59%) of product. mp=199°-201° C.

Workup

  1. customsealed
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. washeluted from a silica column
  5. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-dc7337f55a2c45b78a20c26422ae90f3
Source dataset
uspto-grants-1992_10
Patent number
US05153318

Reaction notes

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