Triethylamine → PD 117519

HRID 2309178Notes

Reaction equation

HRID 2309178 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][CH: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 123445(+-)-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-9c1a808f6df141b7b8c03a27e7b7b33d
Source dataset
uspto-grants-1987_09
Patent number
US04693996

Reaction notes

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