Sodium hydride → 4-chloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)imidazo[4,5-c]-pyridine

HRID 1447000Notes

Reaction equation

HRID 1447000 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]2[N:10]=[CH:11][NH:12][C:8]=2[CH:7]=[CH:6][N:5]=1.[CH2:13]([O:20][C@H:21]1[C@H:25]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:24]([CH2:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:23][C@@H:22]1Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[Cl:3][C:4]1[C:9]2[N:10]=[CH:11][N:12]([C@@H:22]3[O:23][C@H:24]([CH2:34][O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C@@H:25]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@@H:21]3[O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]=2[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53733644-Chloro-1H-imidazo[4,5-c]pyridineHCID 10895454(2R,3R,4S,5R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-chlorotetrahydrofuran

Product 1

HCID 539502144-chloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)imidazo[4,5-c]-pyridineYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.4 g of sodium hydride, 15.4 g of 4-chloro-1H-imidazo[4,5-c]pyridine, and 200 ml of dry dimethylformamide (DMF) is stirred at 50° C. for 5 minutes, cooled, and added to 43.9 g of 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride. The solution is kept at ambient temperature for two hours, concentrated in vacuo, and distributed between a mixture of ethyl acetate-water. Chromatography of the dried ethyl acetate layer over silica gel with 4:1 benzene-ethyl acetate provides 49.6 g of syrupy 4-chloro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazo[4,5-c]-pyridine.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additiondistributed between a mixture of ethyl acetate-water

Sources & evidence

ORD record
ord-e6068d8d6b4e4575bc4ec0350fbc0e16
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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