Sodium Bicarbonate → 2-(4-Methylthiazol-2-ylamino)pyridin-3-ol

HRID 1426087

Reaktionsgleichung

Reaktionsgleichung von HRID 1426087
C([O:8][C:9]1[C:10]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH3:21])[N:20]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>Cl>[CH3:21][C:19]1[N:20]=[C:16]([NH:15][C:10]2[C:9]([OH:8])=[CH:14][CH:13]=[CH:12][N:11]=2)[S:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 166600153-(Benzyloxy)-N-(4-Methyl-1,3-Thiazol-2-Yl)pyridin-2-Amine

Produkt 1

HCID 104656162-(4-Methylthiazol-2-ylamino)pyridin-3-olAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A 250 mL round-bottomed flask was charged 3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (11.4 g, 38.3 mmol) in 6M HCl (100 mL), and the reaction mixture was heated to reflux for 10 hours. The reaction mixture was cooled to room temperature, poured onto ice and saturated sodium bicarbonate, filtered, dried under vacuum and triturated with hexanes to afford 2-(4-methylthiazol-2-ylamino)pyridin-3-ol (6.23 g, 78.5% yield) as a pale yellow solid. 1H NMR (CD3OD) δ 7.79 (dd, 1H), 7.07 (dd, 1H), 6.79 (dd, 1H), 6.46 (q, 1H), 2.28 (s, 3H). LCMS (5 to 95) Rt=2.69 min (apci) m/z=208 (M+H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 10 hours
  3. filtrationfiltered
  4. customdried under vacuum
  5. customtriturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ebd9e6fe969c487da022347defda37f7
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933077B2

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