Isopropanol → (5-Bromo-pyridin-3-yl)-(4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 736334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736334
[Li]CCCC.Br[C:7]1[C:15]2[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=2[N:9]([CH:17]([CH3:19])[CH3:18])[CH:8]=1.[Br:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([CH:32]=1)[C:26](N(OC)C)=[O:27].CC(O)C>CCOCC>[Br:20][C:21]1[CH:32]=[C:25]([C:26]([C:7]2[C:15]3[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=3[N:9]([CH:17]([CH3:19])[CH3:18])[CH:8]=2)=[O:27])[CH:24]=[N:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 457894285-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 86603152(5-Bromo-pyridin-3-yl)-(4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanoneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

n-BuLi (15.3 mL, 2.5 M in Hexane, 38.2 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (10.0 g, 36.4 mmol) in Et2O (300 mL) at −78° C. and stirred for 1 h. 5-Bromo-N-methoxy-N-methyl-nicotinamide (8.9 g, 36.4 mmol) was added to the reaction mixture slowly and stirred for 3 h, warmed to room temperature, and stirred for an additional I h. The reaction mixture was quenched with saturated aqueous NH4Cl (200 mL) and stirred for 20 min. The aqueous layer was extracted with EtOAc (3×300 mL) and the combined organic layers were washed with brine (500 mL), dried (Na2SO4), filtered, and concentrated in vacuo to provide a crude brown solid. Trituration with 2-propanol provided the title compound as a pure off-white solid (7.0 g, 51%). MS: 380.7 (MH+); HPLC Rf: 5.5 min. (HPLC method 4).

Aufarbeitung

  1. stirringstirred for 3 h
  2. stirringstirred for an additional I
  3. customThe reaction mixture was quenched with saturated aqueous NH4Cl (200 mL)
  4. stirringstirred for 20 min
  5. extractionThe aqueous layer was extracted with EtOAc (3×300 mL)
  6. washthe combined organic layers were washed with brine (500 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide a crude brown solid

Quellen und Nachweise

ORD-Eintrag
ord-b48f3a0fb212438fa2310c6f9edd8954
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595325B2

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