Ethanol → HCID 59026635, compound

HRID 333710Notes

Reaction equation

HRID 333710 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH3:16])[C:12]=1[C:13]([NH2:15])=[O:14])=O.[OH-].[Na+].CCO>O>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[C:5]1[NH:15][C:13](=[O:14])[C:12]2[C:11]([CH3:16])=[CH:10][S:9][C:8]=2[N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 590266232-(2-Methoxybenzamido)-4-methylthiophene-3-carboxamide

Product 1

HCID 59026635HCID 59026635, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(2-methoxybenzamido)-4-methylthiophene-3-carboxamide (0.84 g, 2.9 mmol), 6 N aqueous NaOH (4.8 mL), and EtOH (4.8 mL) was heated at 120° C. for 16 h. The reaction was cooled, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under vacuum to give 2-(2-methoxyphenyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one (0.48 g, 61% yield). LC/MS: m/z 273.1 (M+H)+ at 2.91 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with CH2Cl2
  3. washThe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-53353e9a638a47a1b2493809c23b1b61
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

Loading…