Water → Ethyl 3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate

HRID 2307306Notes

Reaction equation

HRID 2307306 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][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:15]([CH3:16])[C:3]=12.[C:24](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[CH3:16][C:15]1[C:3]2[C:2](=[O:1])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]([CH3:24])[C:4]=2[S:13][C:14]=1[CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469718Ethyl 4-hydroxy-3-methyl-2-(morpholin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 22605733Ethyl 3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylateYield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-hydroxy-3-methyl-2-(morpholin-4-ylmethyl)thieno[2,3-b]pyridine-5-carboxylate (Preparation 27, 1.47 g) and potassium carbonate (1.21 g) are suspended be in DMF (25 mL). The mixture is warmed until the ester dissolves and iodomethane (0.30 mL) is added. The reaction mixture is allowed to stir at room temperature for 20 h. The mixture is then poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers are washed with brine (2×25 mL), dried (Na2SO4), and partially concentrated. Hexanes are added and the resulting solid is filtered to afford 0.70 g of the title compound as a light yellow solids Physical characteristics. M.p. 172-173° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.41, 4.19, 3.81, 3.65, 3.59, 2.48, 2.46, 1.27; MS (ESI+) m/z 351 (M+H)+. Anal. Found: C, 58.04; H, 6.54; N, 7.77; S, 8.97.

Workup

  1. dissolutiondissolves
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layers are washed with brine (2×25 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationpartially concentrated
  6. additionHexanes are added
  7. filtrationthe resulting solid is filtered

Sources & evidence

ORD record
ord-a18c3904863e406ea1bd6cf759df9bd5
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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