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

HRID 414175ノート

反応式

HRID 414175 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b40caf6cecd745c1a682da7defadec37
出典データセット
uspto-grants-1988_12
特許番号
US04791103

反応ノート

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