Triethylamine → HCID 13424668, compound

HRID 615864Notes

Reaction equation

HRID 615864 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.Cl.[NH2:21][CH:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1.C(N(CC)CC)C>C(O)C.CO>[CH2:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:30][CH:22]1[NH:21][C:5]1[C:4]2[N:8]=[CH:9][N:10]([C:3]=2[N:2]=[CH:1][N:6]=1)[C@@H:11]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]1[OH:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 1227642-Aminoindan hydrochloride

Product 1

HCID 13424668HCID 13424668, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Two grams 6-chloropurine riboside, 1.48 grams 2-aminoindane hydrochloride and 1.74 g triethylamine are refluxed in ethanol under nitrogen for 20 hours. Upon cooling, solid material crystallizes. The reaction mixture is diluted with 70 ml ethanol, filtered and washed with ethanol. Solid thus obtained is suspended in approximately 25 to 30 ml methanol, filtered, and washed with methanol and dried affording 1.95 g (73%) N(6)-(2-indanyl)adenosine having a melting point of 166°-168° C.

Workup

  1. temperatureUpon cooling
  2. customsolid material crystallizes
  3. additionThe reaction mixture is diluted with 70 ml ethanol
  4. filtrationfiltered
  5. washwashed with ethanol
  6. customSolid thus obtained
  7. filtrationfiltered
  8. washwashed with methanol
  9. customdried

Sources & evidence

ORD record
ord-dd58fa0b0a124fad8745a96c51735f9d
Source dataset
uspto-grants-1985_02
Patent number
US04501735

Reaction notes

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