Methanol → Hypoxanthine

HRID 1976560ノート

反応式

HRID 1976560 の反応式
C(OC1C=C(C=CC=1OC)C[N:13]1[C:21]2[N:20]=[C:19](C(OCC3C=CC=CC=3)(C)C)[NH:18][C:17]=2[C:16](=[O:33])[NH:15][C:14]1=S)C1C=CC=CC=1.C(OC1C=C(C=CC=1OC)CN1C2N=C(C(OCC3C=CC=CC=3)(C)C)NC=2C(=O)N=C1)C1C=CC=CC=1.CO>C(O)CC.[Ni]>[NH:15]1[C:16](=[O:33])[C:17]2[NH:18][CH:19]=[N:20][C:21]=2[N:13]=[CH:14]1

参加物

6

反応物 3

HCID 887MethanolHCID 9914306HCID 9914306、化合物HCID 21998625HCID 21998625、化合物

生成物 1

HCID 135398638Hypoxanthine収率 35.1%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 10311-Propanol溶媒

実験手順

3-(3-Benzyloxy-4-methoxy-benzyl)-8-(1-benzyloxy-1-methyl-ethyl)-2-thioxanthine (26.05 g, 48 mmole) was heated under reflux in 1-propanol (700 ml) with Raney-nickel (29 g) (treated with 0.1% aqueous acetic acid) for 1.5 hours. The nickel was filtered off and the solvent evaporated in vacuo. The residue was dissolved in dichloromethane (300 ml), extracted with sodium carbonate solution and evaporated again to dryness. The residue was dissolved in methanol (150 ml), treated with charcoal, filtered, concentrated and crystallized to give 3-(3-benzyloxy-4-methoxy-benzyl)-8-(1-benzyloxy-1-methyl-ethyl)-hypoxanthine (15.81 g, 64.5%), mp 78-86° C. (containing methanol). A second crop gave 2.29 g (9.3%) of hypoxanthine.

後処理

  1. filtrationThe nickel was filtered off
  2. customthe solvent evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (300 ml)
  4. extractionextracted with sodium carbonate solution
  5. customevaporated again to dryness
  6. dissolutionThe residue was dissolved in methanol (150 ml)
  7. additiontreated with charcoal
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customcrystallized
  11. customto give

出典と根拠

ORDレコード
ord-5e4d8350c5b64a86a59dbb3ab0e03367
出典データセット
uspto-grants-2001_05
特許番号
US06228859B1

反応ノート

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