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

HRID 1426087Notes

Reaction equation

HRID 1426087 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 104656162-(4-Methylthiazol-2-ylamino)pyridin-3-olYield 78.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-ebd9e6fe969c487da022347defda37f7
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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