Formic Acid → HCID 15870903, compound

HRID 430506Notes

Reaction equation

HRID 430506 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[C:12]2[S:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.C(O)=O>[Pd].C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[C:12]2[S:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 2

HCID 284Formic AcidHCID 69711230HCID 69711230, compound

Product 1

HCID 15870903HCID 15870903, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 3-(2-chloro-phenyl)-2-[2-pyrid-2-yl-vinyl]-3H-thieno[3,2-d]pyrimidin-4-one (0.12 g, 0.33 mmol), ethanol, 10 mL), formic acid (0.55 mL, 14.8 mmol) and 10% palladium on carbon (0.12 g) was refluxed 4 hours, cooled and diluted with ethanol and water. The mixture was filtered through Celite® (trademark) and the pad was rinsed with ethyl acetate and water. The filtrate was treated with saturated aqueous sodium bicarbonate and the phases were separated. The aqueous layer was extracted with ethyl acetate and the combined organic phase was washed with water and brine, dried over sodium sulfate, and concentrated to afford 0.094 g of 3-(2-chloro-phenyl)-2-(2-pyridin-2-yl-ethyl)-3H-thieno[3,2-d]pyrimidin-4-one as a tan film. The material was dissolved in dioxane (3 mL) and treated with ether saturated with hydrogen chloride. The solid was collected and weighed 0.094 g. The solid was taken up in water, concentrated, and azeotropically dried by suspending the product in chloroform and concentrating three times to yield 3-(2-chloro-phenyl)-2-(2-pyridin-2-yl-ethyl)-3H-thieno[3,2-d]pyrimidin-4-one hydrochloride (0.038 g, 31%) as a yellow solid.

Workup

  1. temperaturewas refluxed 4 hours
  2. temperaturecooled
  3. filtrationThe mixture was filtered through Celite® (trademark)
  4. washthe pad was rinsed with ethyl acetate and water
  5. additionThe filtrate was treated with saturated aqueous sodium bicarbonate
  6. customthe phases were separated
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. washthe combined organic phase was washed with water and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c4846fadc8764934ad69397fe87cae2e
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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