Triethylamine → N6-[2,3-dihydro-1H-inden-1-yl]methyl-adenosine

HRID 414173Notes

Reaction equation

HRID 414173 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.[CH:20]1([CH2:29][NH2:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1.C(N(CC)CC)C>C(O)C>[CH:20]1([CH2:29][NH:30][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:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 143486922,3-dihydro-1H-inden-1-ylmethanamine

Product 1

HCID 14348694N6-[2,3-dihydro-1H-inden-1-yl]methyl-adenosineYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.0 g of 6-chloropurine riboside, 2.0 g of 1-indanylmethylamine as prepared in Example A hereinafter and 3.18 g of triethylamine are refluxed in 75 ml of absolute ethanol under nitrogen for 24 hours. The reaction is cooled to room temperature, precipitated nucleoside is filtered, washed with ethanol and dried affording 2.78 g (67%) of N6 -[2,3-dihydro-1H-inden-1-yl]methyl-adenosine having a melting point of 137°-139° C. Anals. calcd. for C20H23N5O4 ; Found: C=60.44; H=5.83; N=17.62 C=60.81; H=5.70; N=17.35.

Workup

  1. customprecipitated nucleoside
  2. filtrationis filtered
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-8db04e701b1f4b928df61376ff2c8c63
Source dataset
uspto-grants-1988_12
Patent number
US04791103

Reaction notes

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