Triethylamine → N6-[(1,2-Dihydro-1-acenaphthylenyl)methyl]adenosine

HRID 652711Notes

Reaction equation

HRID 652711 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.C(N(CC)CC)C.[CH:27]1([CH2:39][NH2:40])[C:37]2=[C:38]3[C:33](=[CH:34][CH:35]=[CH:36]2)[CH:32]=[CH:31][CH:30]=[C:29]3[CH2:28]1>C(O)C>[CH:27]1([CH2:39][NH:40][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:37]2=[C:38]3[C:33](=[CH:34][CH:35]=[CH:36]2)[CH:32]=[CH:31][CH:30]=[C:29]3[CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 105593731,2-Dihydro-1-acenaphthylenylmethylamine

Product 1

HCID 68114916N6-[(1,2-Dihydro-1-acenaphthylenyl)methyl]adenosineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Six chloropurine riboside (1.7 g, 6 mmol), triethyl amine (1.5 g, 15 mmol) and the N-[(1,2-dihydro-1-acenaphthylenyl)methyl]amine, B, as prepared in the following Example B (1.4 g, 6.4 mmol) were stirred at reflux in ethanol (100 ml) overnight. The solution was cooled to room temperature and filtered free of solid. The solution was washed with ethanol (50 ml) and dried at 65° C. in vacuo for four hours, to give 2.2 g (85%) of a white solid, mp 173°-175° C. Anal. (C23H23N5O4); calc: C=63.73, H=5.35, N=16.16; found: C=63.55, H=5.49, N=16.00.

Workup

  1. filtrationfiltered free of solid
  2. washThe solution was washed with ethanol (50 ml)
  3. customdried at 65° C. in vacuo for four hours

Sources & evidence

ORD record
ord-a9288f49c23d46329d7ef8c54c470571
Source dataset
uspto-grants-1987_06
Patent number
US04673670

Reaction notes

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