1,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate → 3-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 1366711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366711
[N:1]1[C:9]2[CH:8]=[N:7][CH:6]=[N:5][C:4]=2[N:3]([CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)[N:2]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[CH2:10][N:3]1[C:4]2[N:5]=[CH:6][N:7]=[CH:8][C:9]=2[N:1]=[N:2]1

Komponenten

4

Edukt 1

HCID 669363511,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate

Produkt 1

HCID 669365273-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate (1.98 g, 6.54 mmol) was dissolved in a mixture of CH2Cl2 (10 mL) and TFA (2.5 mL) and allowed to stir at room temperature overnight. When the reaction was complete as determined by LCMS, the solution was concentrated in vacuo, and the residue was dissolved in CH2Cl2 (5 mL) and washed with 1 N aq. NaOH (30 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo to provide 3-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidine (758 mg, 57%). LCMS: (M+H)+: 205.1.

Aufarbeitung

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (5 mL)
  3. washwashed with 1 N aq. NaOH (30 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9f33368b545548d5873e31a30239eb78
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

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