((2S,3S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-3-azidotetrahydrofuran-2-yl)methanol → Trans-2-amino-9-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-6((2-phenylcyclopropyl)amino)-9H-purine

HRID 465729Notes

Reaction equation

HRID 465729 reaction equation
Cl.[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([N:29]=[N+:30]=[N-:31])[CH2:23]2)=[C:15](Cl)[N:14]=1>O>[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[C@@H:22]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([N:29]=[N+:30]=[N-:31])[CH2:23]2)=[C:15]([NH:11][C@@H:9]2[CH2:10][C@H:8]2[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:14]=1

Participants

4

Reactant 2

HCID 476464((2S,3S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-3-azidotetrahydrofuran-2-yl)methanolHCID 2723716Tranylcypromine hydrochloride

Product 1

HCID 86746176Trans-2-amino-9-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-6((2-phenylcyclopropyl)amino)-9H-purine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Trans-2-phenylcyclopropylamine hydrochloride (Aldrich, lot #01903MK, 2.5 g, 14.7 mmol) was dissolved in 5 mL H2O and the pH adjusted to pH 12. The aqueous solution was extracted with 10 mL EtOAc. The EtOAc was evaporated to dryness and dissolved in 25 mL EtOH. 2-Amino-9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6-chloro-9H-purine (Example 3d) (0.4 g, 1.29 mmol) was added to the ethanolic solution then placed in a sealed tube and heated at 50° C. for 18 hours. The solvents were removed in vacuo to yield a dark oil. The oil was chromatographed on basic alumina eluted with 1% MeOH in CHCl3. The impure product fractions were combined, evaporated, and rechromatographed on silica gel eluted with 5% MeOH in CHCl3. The collected impure product was again applied to basic alumina eluted with 1% MeOH in CHCl3 to give, after combination and evaporation of appropriate fractions, 0.0802 g (0.2 mMol, 15.5%); mp=65°-70°C.

Workup

  1. extractionThe aqueous solution was extracted with 10 mL EtOAc
  2. customThe EtOAc was evaporated to dryness
  3. dissolutiondissolved in 25 mL EtOH
  4. customthen placed in a sealed tube
  5. customThe solvents were removed in vacuo
  6. customto yield a dark oil
  7. customThe oil was chromatographed on basic alumina
  8. washeluted with 1% MeOH in CHCl3
  9. customevaporated
  10. customrechromatographed on silica gel
  11. washeluted with 5% MeOH in CHCl3
  12. washeluted with 1% MeOH in CHCl3
  13. customto give
  14. customafter combination and evaporation of appropriate fractions, 0.0802 g (0.2 mMol, 15.5%)

Sources & evidence

ORD record
ord-a9cbbd620eb046e5918cace6eb0c8310
Source dataset
uspto-grants-1992_10
Patent number
US05153318

Reaction notes

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