Pivaloyl chloride → HCID 178447243, Verbindung

HRID 1510920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510920
[NH2:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:11])[N:3]=1.[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[Cl:11][C:4]1[N:3]=[C:2]([NH:1][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[NH:7][C:6]2=[N:8][CH:9]=[CH:10][C:5]=12

Komponenten

4

Edukt 2

HCID 62493Pivaloyl chlorideHCID 178508434HCID 178508434, Verbindung

Produkt 1

HCID 178447243HCID 178447243, VerbindungAusbeute 110,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirring solution of 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine (7.3 g, 43.61 mmol) in anhydrous pyridine (120 mL) was added pivaloyl chloride (18.7 mL, 152.63 mmol). The reaction was stirred at RT under nitrogen for 16 h and quenched with MeOH (50 mL). The solvents were then removed in vacuo, and the residue was co-evaporated with toluene (100 mL). The resulting residue was dissolved in EtOAc (150 mL) and washed with 0.1 M HCl (3×75 mL). The organic layer was dried (MgSO4) and evaporated. The crude material was resolved by silica chromatography (30% EtOAc/hexane) to yield 9a (12.2 g) as a white crystalline solid.

Aufarbeitung

  1. customquenched with MeOH (50 mL)
  2. customThe solvents were then removed in vacuo
  3. dissolutionThe resulting residue was dissolved in EtOAc (150 mL)
  4. washwashed with 0.1 M HCl (3×75 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-58eb44f798ba4bdca0709d104ae3db8a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212020B2

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