Sodium Iodide → (1S,2R,3R,5R)-3-(hydroxymethyl)-5-[(6-iodopyrimidin-4-yl)amino]cyclopentane-1,2-diol

HRID 1397568ノート

反応式

HRID 1397568 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@@H:9]2[CH2:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]2[OH:17])[CH:3]=1.[I-:18].[Na+]>I>[OH:15][CH2:14][C@H:12]1[CH2:13][C@@H:9]([NH:8][C:4]2[CH:3]=[C:2]([I:18])[N:7]=[CH:6][N:5]=2)[C@H:10]([OH:17])[C@@H:11]1[OH:16]

参加物

4

反応物 2

HCID 5238Sodium IodideHCID 59671293(1R,2S,3R,5R)-3-[(6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)cyclopentane-1,2-diol

生成物 1

HCID 86663353(1S,2R,3R,5R)-3-(hydroxymethyl)-5-[(6-iodopyrimidin-4-yl)amino]cyclopentane-1,2-diol収率 944.2%

試薬・触媒・溶媒 1

HCID 24841Hydrogen iodide溶媒

反応条件

温度
70 °C

実験手順

To a solution of (1R,2S,3R,5R)-3-[(6-chloropyrimidin-4-yl)amino]-5-(hydroxymethyl)cyclopentane-1,2-diol (1.880 g, 7.239 mmol) in hydroiodic acid (23.9 mL) was added sodium iodide (5.42 g, 36.2 mmol). The mixture heated to 70° C. for 10 min then concentrated and azeotroped using toluene (3×). The residue was dissolved in acetone and NaHCO3 was added. The suspension was filtered and the filtrate was concentrated in vacuo to obtain the title compound (24 g, >99%). LC/MS: Rt=0.76 min ES+ 352 (FA standard).

後処理

  1. concentrationthen concentrated
  2. customazeotroped
  3. dissolutionThe residue was dissolved in acetone
  4. additionNaHCO3 was added
  5. filtrationThe suspension was filtered
  6. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-2538908fa6114e1fa2b9c39515d04de6
出典データセット
uspto-grants-2014_12
特許番号
US08901136B2

反応ノート

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