((2S,3S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-3-azidotetrahydrofuran-2-yl)methanol → 3'-Azido-2,6-diaminopurine-2',3'-dideoxyriboside

HRID 2408268Notes

Reaction equation

HRID 2408268 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.[NH3:22].CO>>[N:18]([C@H:13]1[CH2:12][C@H:11]([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([NH2:1])=[N:3][C:4]=3[NH2:22])[O:15][C@@H:14]1[CH2:16][OH:17])=[N+:19]=[N-:20]

Participants

3

Reactant 2

HCID 476464((2S,3S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-3-azidotetrahydrofuran-2-yl)methanolHCID 21705897Ammonia methanol

Product 1

HCID 721823'-Azido-2,6-diaminopurine-2',3'-dideoxyribosideYield 58%

Conditions

Temperature
80 °C

Procedure

A mixture of compound 77 (190 mg, 0.61 mmol) and NH3/CH3OH (30 mL) was heated to 80° C. at seal bomb for 18 h, then cooled to room temperature. The reaction mixture was evaporated and purified by flash column chromatography with dichloromethane:ethyl acetate:methanol=7:7:1 to obtain the white solid 100 mg 58%.

Workup

  1. customat seal bomb for 18 h
  2. temperaturecooled to room temperature
  3. customThe reaction mixture was evaporated
  4. custompurified by flash column chromatography with dichloromethane

Sources & evidence

ORD record
ord-36a32f448df84fb3bf88f6eef23ab399
Source dataset
uspto-grants-2014_08
Patent number
US08815829B2

Reaction notes

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