Iodine → 1-β-D-Arabinofuranosyl-5-iodo-2,4(1H,3H)-pyrimidinedione

HRID 1050276ノート

反応式

HRID 1050276 の反応式
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].[I:18]I.[N+]([O-])(O)=O>C(Cl)(Cl)Cl>[C@@H:1]1([N:10]2[CH:17]=[C:16]([I:18])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]

参加物

5

反応物 3

HCID 807IodineHCID 944Nitric AcidHCID 18323Uracil Arabinoside

生成物 1

HCID 966211-β-D-Arabinofuranosyl-5-iodo-2,4(1H,3H)-pyrimidinedione収率 62%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A mixture of 15 (1.2 g, 4.9 mmol), iodine (1.50 g, 5.9 mmol), CHCl3 (6 mL), and 1 N HNO3 (24 mL) was heated at reflux for 2 hours, and then cooled. The crystalline solid was collected by filtration and washed with ether to give the title compound 16 as a white solid (1.12 g, 62%). 1H NMR (DMSO-d6) δ 11.6 (s, 1H, NH), 8.10 (s, 1H, H-6), 5.95 (d, 1H, H-1′), 5.52 (br, 1H, OH), 5.40-5.10 (br, 1H, OH), 4.15-3.90 (m, 2H, H-2′, H-3′), 3.80-3.60 (m, 3H, H-4′, H-5′), 3.60-3.30 (m, 1H, OH).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. filtrationThe crystalline solid was collected by filtration
  5. washwashed with ether

出典と根拠

ORDレコード
ord-bb1c205c06744f0da34a4d4889afe25d
出典データセット
uspto-grants-2016_07
特許番号
US09382286B2

反応ノート

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