Hydrochloric Acid → (7-Chloro-2,6-naphthyridin-3-yl)methanol

HRID 468896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468896
Cl.[Si]([O:9][CH2:10][C:11]1[N:12]=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][N:17]=[C:16]([Cl:21])[CH:15]=2)(C(C)(C)C)(C)C>O.CO.C(Cl)Cl.CCCCCCC>[Cl:21][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[C:11]([CH2:10][OH:9])[N:12]=[CH:13]2)=[CH:18][N:17]=1

Komponenten

7

Edukt 2

HCID 313Hydrochloric AcidHCID 866749683-((Tert-butyldimethylsilyloxy)methyl)-7-chloro-2,6-naphthyridine

Produkt 1

HCID 86674969(7-Chloro-2,6-naphthyridin-3-yl)methanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

A solution of 5.0M hydrogen chloride in water (0.73 mL) was added to a solution of 3-((tert-butyldimethylsilyloxy)methyl)-7-chloro-2,6-naphthyridine (1.13 g, 3.7 mmol) in methanol (15 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with methylene chloride (150 mL), and washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was suspended in heptane (10 mL) and filtered to provide the title compound as a white powder (645 mg, 90%). 1H NMR (400 MHz, DMSO) δ 9.37 (s, 2H), 8.23 (s, 1H), 8.06 (s, 1H), 5.65 (t, J=5.6 Hz, 1H), 4.78 (d, J=5.6 Hz, 2H).

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a residue that
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-cb9909c15964465e87787467b5c86ddc
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623889B2

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