Triethylamine → HCID 13686253, compound

HRID 1380505Notes

Reaction equation

HRID 1380505 reaction equation
Cl[C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]1[OH:14].[C:21]1([CH:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:28][NH2:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C(O)C>[C:30]1([CH:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:28][NH:29][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[C:9]([NH2:11])[N:10]=2)[C@@H:12]2[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]2[OH:14])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775752,2-DiphenylethylamineHCID 1021972004-07-1

Product 1

HCID 13686253HCID 13686253, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.25 g of 6-chloro-2-amino-9-(β-D-ribofuranosyl)purine, 0.899 g of 2,2-diphenylethylamine and 0.503 g of triethylamine is heated under reflux in 30 ml of absolute ethanol under a nitrogen atmosphere for 18 hours. The solvent is evaporated to dryness and residue is treated with 50 ml of cold water. The insoluble organic material is filtered, dried, and purified by medium pressure liquid chromatography on silica gel. The product is eluted with 10% methanol-chloroform. Evaporation of the solvent from the pure fractions affords a colorless solid material. Crystallization from a mixture of CHCl3 -2-propanol (10:1) and hexane affords N6 -(2,2-diphenylethyl)-2-aminoadenosine, mp 134°-137° C.

Workup

  1. temperatureis heated
  2. customThe solvent is evaporated to dryness and residue
  3. additionis treated with 50 ml of cold water
  4. filtrationThe insoluble organic material is filtered
  5. customdried
  6. custompurified by medium pressure liquid chromatography on silica gel
  7. washThe product is eluted with 10% methanol-chloroform
  8. customEvaporation of the solvent from the pure fractions
  9. customaffords a colorless solid material
  10. customCrystallization
  11. additionfrom a mixture of CHCl3 -2-propanol (10:1) and hexane

Sources & evidence

ORD record
ord-786619ef94564f859c70bb8d4a0f5306
Source dataset
uspto-grants-1986_04
Patent number
US04582823

Reaction notes

Loading…