Hydrochloric Acid → Ethyl 5-cyanomethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate

HRID 606500Notes

Reaction equation

HRID 606500 reaction equation
Br[CH2:2][C:3]1[C:11]2[C:10](=[O:12])[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:7][C:6]=2[S:5][CH:4]=1.[C-:18]#[N:19].[Na+].Cl>CN(C=O)C>[C:18]([CH2:2][C:3]1[C:11]2[C:10](=[O:12])[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:7][C:6]=2[S:5][CH:4]=1)#[N:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 58103632Ethyl 5-(bromomethyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate

Product 1

HCID 57708728Ethyl 5-cyanomethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylateYield 18.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 5-(bromomethyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate (2000 mg, 6.31 mmol) in DMF (10 mL) was added sodium cyanide (649 mg, 13.2 mmol) at room temperature, and the mixture was stirred for 12 hr. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as a pale-brown powder (300 mg, 18%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-d1241b60cb5142faae8f2c190d494c39
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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