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

HRID 1747623노트

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HRID 1747623 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 24841Hydrogen iodide용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-523f417bd7394131bb2f59f5ca85251f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150525B2

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