Triethylamine → N(6)-methyl-N(6)-but-2-enyl-adenosine

HRID 328194ノート

反応式

HRID 328194 の反応式
C([N:4]1[C:12]2[CH:7]([N:8](C(=O)C)[CH2:9][N:10](C(=O)C)[C:11]=2Cl)[N:6]([C@@H:20]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]2[OH:22])[CH2:5]1)(=O)C.[CH3:29][NH:30][CH2:31][CH:32]=[CH:33][CH3:34].C(N(CC)CC)C>C(O)(C)C>[CH3:29][N:30]([CH2:31][CH:32]=[CH:33][CH3:34])[C:11]1[C:12]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[CH:9][N:10]=1)[C@@H:20]1[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]1[OH:22]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 53970299Methyl-but-2-enylamineHCID 131710375Triacetyl-6-chloro-9-(beta-D-ribofuranosyl)-purine

生成物 1

HCID 54015847N(6)-methyl-N(6)-but-2-enyl-adenosine収率 70%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

7.3 g. triacetyl-6-chloro-9-(β-D-ribofuranosyl)-purine, 2.1 g. methyl-but-2-enylamine and 2.8 ml. triethylamine were heated under reflux for 2 hours in 100 ml. isopropanol. After cooling, the reaction mixture was mixed with 200 ml. diethyl ether, extracted twice with water and the organic phase evaporated to dryness in a vacuum. The residue was dissolved in 100 ml. 25% methanolic ammonia and then left to stand overnight at ambient temperature. The solution was thereafter evaporated and the residue obtained was recrystallized from water. 4.1 g. (70% of theory) N(6)-methyl-N(6)-but-2-enyl-adenosine were obtained; m.p. 160° - 162° C.

後処理

  1. temperatureunder reflux for 2 hours in 100 ml
  2. temperatureAfter cooling
  3. additionthe reaction mixture was mixed with 200 ml
  4. extractiondiethyl ether, extracted twice with water
  5. customthe organic phase evaporated to dryness in a vacuum
  6. dissolutionThe residue was dissolved in 100 ml
  7. wait25% methanolic ammonia and then left
  8. customThe solution was thereafter evaporated
  9. customthe residue obtained
  10. customwas recrystallized from water

出典と根拠

ORDレコード
ord-23e71be60a3c4d52aa305eab88aec069
出典データセット
uspto-grants-1977_04
特許番号
US04016262

反応ノート

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