Isopropanol → HCID 7083849, compound

HRID 1981296Notes

Reaction equation

HRID 1981296 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13].[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][NH2:24].CN(C)C=O.C(O)(C)C>C(N(CC)CC)C>[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][NH:24][C:2]1[C:3]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[CH:9][N:10]=1)[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6228DimethylformamideHCID 666482-ChlorobenzylamineHCID 930036-Chloropurine riboside

Product 1

HCID 7083849HCID 7083849, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 28.6 g of 6-chloro-9(β-D-ribofuranosyl)-purine, 14.2 g of o-chlorobenzyl amine, 400 ml of dimethylformamide, 400 ml of isopropanol and 50 ml of triethylamine is left to stand at 20° for 4 days. The mixture is evaporated, the residue is dissolved in chloroform, the chloroform solution is washed with 1% aqueous acetic acid and evaporated again and the residue is triturated with ether to give N6 -o-chlorobenzyl-adenosine (Ia). M.p.: 182°-183°.

Workup

  1. waitis left
  2. customThe mixture is evaporated
  3. dissolutionthe residue is dissolved in chloroform
  4. washthe chloroform solution is washed with 1% aqueous acetic acid
  5. customevaporated again
  6. customthe residue is triturated with ether

Sources & evidence

ORD record
ord-7f8573671bb947ef8c8359d1375ca38d
Source dataset
uspto-grants-1985_04
Patent number
US04514405

Reaction notes

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