Ammonia → HCID 54030984, compound

HRID 1447006Notes

Reaction equation

HRID 1447006 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][N:6]([C@@H:11]2[O:31][C@H:30]([CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:12]2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]=1[CH2:8][C:9]#[N:10])#[N:2].[NH3:41]>CO>[NH2:2][C:1]1[C:3]2[N:4]=[CH:5][N:6]([C@@H:11]3[O:31][C@H:30]([CH2:32][O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C@@H:21]([O:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C@@H:12]3[O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:7]=2[CH:8]=[C:9]([NH2:41])[N:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54238159HCID 54238159, compound

Product 1

HCID 54030984HCID 54030984, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6.0 g of 4-cyano-5-cyanomethyl-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazole and 300 ml of dry methanol saturated at 0° C. with ammonia is kept in a steel bomb at ambient temperatures for 24 hours and then evaporated in vacuo to dryness. The residue is triturated with ether, dissolved in methanol, absorbed on silica gel, and chromatographed over silica gel with chloroform-methanol (10:1) to provide 4.0 g of 4,6-diamino-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazo[4,5-c]pyridine.

Workup

  1. customevaporated in vacuo to dryness
  2. customThe residue is triturated with ether
  3. dissolutiondissolved in methanol
  4. customabsorbed on silica gel
  5. customchromatographed over silica gel with chloroform-methanol (10:1)

Sources & evidence

ORD record
ord-06e4a4c093a74eecbecd7e2600882be6
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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