Water → Ethyl 4-hydroxy-3-methyl-2-(morpholin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxylate

HRID 2307305Notes

Reaction equation

HRID 2307305 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[S:13][CH:14]=[C:15]([CH3:16])[C:3]=12.[Cl-].[CH2:18]=[N+:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.O.C(=O)(O)[O-].[Na+]>C(#N)C>[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[S:13][C:14]([CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:15]([CH3:16])[C:3]=12

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 11367014Morpholinium, 4-methylene-, chlorideHCID 178469714Ethyl 3-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 178469718Ethyl 4-hydroxy-3-methyl-2-(morpholin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxylateYield 96.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of ethyl 4-hydroxy-3-methylthieno[2,3-b]pyridine-5-carboxylate (Preparation 26, 0.92 g) and 4-methylenemorpholin-4-ium chloride (1.57 g) in acetonitrile (40 mL) is heated to 60° C. for 4 h. The resulting suspension is allowed to cool to room temperature, poured into water, and adjusted to neutral pH with saturated aq. sodium bicarbonate. The solution is extracted with CH2Cl2 (3×100 mL). The combined organic layers are washed with brine (25 mL), dried (Na2SO4), and concentrated to afford 1.26 g of the title compound as a yellow solid. Physical characteristics. M.p. 182-185° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.64, 4.37, 3.70, 3.38, 2.51, 2.47, 1.35; MS (ESI−) m/z 335 (M-H). Anal. Found. C, 56.93; H, 6.10; N, 8.26; S, 9.34.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe solution is extracted with CH2Cl2 (3×100 mL)
  3. washThe combined organic layers are washed with brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-116b457e0db14855b052c9d5a79a5f13
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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