Ethanol → 2-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 333701Notes

Reaction equation

HRID 333701 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[C:5]([NH:7][C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:13]([NH2:15])=[O:14])=O.[OH-].[Na+].CCO>O>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[C:5]1[NH:15][C:13](=[O:14])[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 590266413-(2-Methoxybenzamido)thiophene-2-carboxamide

Product 1

HCID 1359915042-(2-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-oneYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-(2-methoxybenzamido)thiophene-2-carboxamide (1.4 g, 5.0 mmol), 6 N aqueous NaOH (8 mL), and EtOH (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)thieno[3,2-d]pyrimidin-4(3H)-one (0.80 g, 62% yield). LC/MS: m/z 259.3 (M+H)+ at 2.32 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-a86392b889cb4a84acbf55a44e2eda64
Source dataset
uspto-grants-2014_11
Patent number
US08883781B2

Reaction notes

Loading…