Hydrochloric Acid → 2-methyl-3H,4H-thieno[2,3-d]pyrimidin-4-one

HRID 718306Notes

Reaction equation

HRID 718306 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]CC)=O.[C:12](#[N:14])[CH3:13].Cl>O1CCOCC1>[CH3:13][C:12]1[NH:14][C:7](=[O:9])[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 1988156Ethyl 2-aminothiophene-3-carboxylate

Product 1

HCID 15370652-methyl-3H,4H-thieno[2,3-d]pyrimidin-4-oneYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of ethyl 2-aminothiophene-3-carboxylate (0.1 g, 0.64 mmol) and acetonitrile (50 μl, 0.95 mmol) in dioxane (3 ml) was added 4M HCl in dioxane (3 ml). The mixture was stirred at room temperature overnight. The solvents were removed under reduced pressure. The residue was diluted with water and made alcaline with a saturated aqueous sodium bicarbonate solution. The precipitate was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 50:1) to yield the title compound as a white solid (42 mg, 40%).

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customThe crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 50:1)

Sources & evidence

ORD record
ord-0bc7a3dd716f42f28b34ef035c42df44
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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