Butylamine → [(2S,3S,5R)-5-[2-amino-6-(butylamino)purin-9-yl]-3-azido-tetrahydrofuran-2-yl]methanol

HRID 465728Notes

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]([NH2:26])[CH2:23][CH2:24][CH3:25]>CO>[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:26][CH2:22][CH2:23][CH2:24][CH3:25])[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Amino-9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6-chloro-9H-purine (Example 3d) (0.40 g, 1.29 mmol) and n-butylamine (Aldrich, #06221JP, 1.28mL, 12.9 mmol) were combined in 25 mL MeOH and placed in a sealed tube. The reaction was heated at 60° C. for 18 hours followed by evaporation of the solvents. Chromatography of the residue on basic alumina eluted with 2% MeOH in CHCl3 gave, after combination and evaporation of appropriate fractions, 0.279 g (0.8 mMol. 62.3%); mp=44°-47°C.

Workup

customplaced in a sealed tube
customfollowed by evaporation of the solvents
washChromatography of the residue on basic alumina eluted with 2% MeOH in CHCl3
customgave
customafter combination and evaporation of appropriate fractions, 0.279 g (0.8 mMol. 62.3%)

Sources & evidence

ORD record: ord-6b1dee76b87d4e7abce10a6734033f38
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05153318

Reaction notes

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