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

HRID 447630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447630
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 86663353(1S,2R,3R,5R)-3-(hydroxymethyl)-5-[(6-iodopyrimidin-4-yl)amino]cyclopentane-1,2-diolAusbeute 944,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24841Hydrogen iodideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3be66c126c88470782f5fb75d6329236
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481550B2

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