Triethylamine → 3-[2-(4-methoxyphenyl)-2-oxoethyl]-6-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1889396Notes

Reaction equation

HRID 1889396 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:11])=[CH:5][C:6]=1[C:7]([O:9]C)=O.Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.Cl.[NH2:32][CH2:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[O:35]>C(Cl)Cl>[CH3:43][O:42][C:39]1[CH:40]=[CH:41][C:36]([C:34](=[O:35])[CH2:33][N:32]2[C:7](=[O:9])[C:6]3[CH:5]=[C:4]([CH3:11])[S:3][C:2]=3[NH:1][C:13]2=[O:15])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 675878Methyl-2-amino-5-methyl-3-thiophenecarboxylateHCID 124871882-Amino-4'-methoxyacetophenone hydrochloride

Product 1

HCID 593515903-[2-(4-methoxyphenyl)-2-oxoethyl]-6-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 176.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (100 mL) of methyl 2-amino-5-methylthiophene-3-carboxylate (2 g) in methylene chloride were added triphosgene (1.5 g) and triethylamine (4.24 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture were further added triethylamine (1.8 mL) and 2-amino-1-(4-methoxyphenyl)ethanone hydrochloride (2.6 g), and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (100 mL), sodium methoxide (3.16 g) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with 1N hydrochloric acid and chloroform. The chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (2.94 g, 76%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in methanol (100 mL)
  6. additionsodium methoxide (3.16 g) was added
  7. stirringthe mixture was stirred at 60° C. for 2 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. extractionthe obtained residue was extracted with 1N hydrochloric acid and chloroform
  10. washThe chloroform layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-254ff9af9d7a4367b3dac3842ad7daa3
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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