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

HRID 65444

Reaction equation

HRID 65444 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-322d46cc4d104fd9b4911580e2e43df7
Source dataset
uspto-grants-1986_09
Patent number
US04614732

Linked notes

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