Diisopropyl azodicarboxylate → tert-butyl (2S)-2-([4-amino-3-iodo-1H-pyrazolo[3,4-d]-pyrimidin-1-yl]methyl)-4,4-difluoropyrrolidine-1-carboxylate

HRID 1529935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529935
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[F:12][C:13]1([F:27])[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:15]([CH2:25]O)[CH2:14]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH2:25][C@@H:15]3[CH2:14][C:13]([F:27])([F:12])[CH2:17][N:16]3[C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[N:3]=[C:2]([I:1])[C:10]=12

Komponenten

5

Edukt 3

HCID 5363146Diisopropyl azodicarboxylateHCID 20648576tert-Butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 178508725HCID 178508725, Verbindung

Produkt 1

HCID 86714507tert-butyl (2S)-2-([4-amino-3-iodo-1H-pyrazolo[3,4-d]-pyrimidin-1-yl]methyl)-4,4-difluoropyrrolidine-1-carboxylateAusbeute 20,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under nitrogen, to a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.61 g, 10.00 mmol, 1.00 equiv), tert-butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate (2.37 g, 9.99 mmol, 1.00 equiv) and TPP (4 g, 15.2 mmol, 1.50 equiv) in THF was DIAD (3.00 g, 15.0 mmol, 1.50 equiv) at 0° C. in 30 min. The resulting solution was stirred overnight at room temperature. The mixture was then concentrated under vacuum and the residue was applied onto a silica gel column with dichloromethane/ethyl acetate (3/1) to give 1 g of tert-butyl (2S)-2-([4-amino-3-iodo-1H-pyrazolo[3,4-d]-pyrimidin-1-yl]methyl)-4,4-difluoropyrrolidine-1-carboxylate as reddish oil.

Aufarbeitung

  1. customat 0° C.
  2. customin 30 min
  3. concentrationThe mixture was then concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-05a80df6b81144e5948073039d686f33
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090621B2

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