Triethylamine → PD 117519

HRID 615866Notes

Reaction equation

HRID 615866 reaction equation
[CH:1]1[N:6]=[C:5](Cl)[C:4]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[C:3]=2[N:2]=1.[NH2:20][C@H:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1.C(N(CC)CC)C>C(O)C>[C@H:21]1([NH:20][C:5]2[C:4]3[N:8]=[CH:9][N:10]([C:3]=3[N:2]=[CH:1][N:6]=2)[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]2[OH:19])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 2733933(R)-(-)-1-Aminoindan

Product 1

HCID 13424663PD 117519Yield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

For 20 hours, 1.83 g 6-chloropurine riboside, 0.95 g (R)(-)-1-aminoindane and 0.862 g triethylamine are refluxed in 50 ml absolute ethanol under nitrogen atmosphere. The solvent is evaporated to dryness and residue is treated with 50 ml cold water. The solid material is filtered, dissolved in excess ethanol, and volatiles are evaporated under reduced pressure to remove water. Residue upon treatment with ethanol affords solid material. It is filtered and dried. One more crop of the same material is obtained from the mother liquor yielding 1.46 g (60% of theory) of N(6) [1-(R)-indanyl]adenosine having a melting point of 185°-187° C.

Workup

  1. customThe solvent is evaporated to dryness and residue
  2. additionis treated with 50 ml cold water
  3. filtrationThe solid material is filtered
  4. dissolutiondissolved in excess ethanol
  5. customvolatiles are evaporated under reduced pressure
  6. customto remove water
  7. customResidue upon treatment with ethanol affords solid material
  8. filtrationIt is filtered
  9. customdried
  10. customOne more crop of the same material is obtained from the mother liquor

Sources & evidence

ORD record
ord-ea0f9c2ec7de4abd8ec2cb77a58a068c
Source dataset
uspto-grants-1985_02
Patent number
US04501735

Reaction notes

Loading…