Triethylamine → N6-[1,2,3,4-tetrahydro-1-hydroxy-1-naphthalenyl]methyl adenosine

HRID 414175Notes

Reaction equation

HRID 414175 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.[OH:20][C:21]1([CH2:31][NH2:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C(O)C>[OH:20][C:21]1([CH2:31][NH:32][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:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 129148591-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 14348644N6-[1,2,3,4-tetrahydro-1-hydroxy-1-naphthalenyl]methyl adenosineYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction mixture of 1.7 g of 6-chloropurine riboside, 1.7 g of (1,2,3,4-tetrahydro-1-hydroxynaphthyl)methyamine as prepared in Example B hereinafter and 2.0 g of triethylamine is refluxed in 150 ml ethanol for 24 hours. Volatiles are evaporated to dryness and residue is treated with 150 ml of cold water. Clear aqueous solution is decanted off. The water treatment is repeated twice followed by dissolving the residue in methanol and evaporating it to dryness. Co-evaporation several times with methanol affords solid material. It is dried under reduced pressure yielding 2.2 g (85%) of N6 -[1,2,3,4-tetrahydro-1-hydroxy-1-naphthalenyl]methyl adenosine having a melting point of 110°-115° C. Anals. calcd. for C21H25N5O5.0.5 C2H5OH, Found: C=58.65; H=6.26, N=15.55, C=59.27; H=6.34; N=15.53.

Workup

  1. customVolatiles are evaporated to dryness and residue
  2. additionis treated with 150 ml of cold water
  3. customClear aqueous solution is decanted off
  4. dissolutionby dissolving the residue in methanol
  5. customevaporating it to dryness
  6. customCo-evaporation several times with methanol
  7. customaffords solid material
  8. customIt is dried under reduced pressure

Sources & evidence

ORD record
ord-b40caf6cecd745c1a682da7defadec37
Source dataset
uspto-grants-1988_12
Patent number
US04791103

Reaction notes

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