Acetic Acid → 3,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1775604

Reaction equation

HRID 1775604 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][S:4][C:3]=1[C:13]([O:15]C)=O.[CH:17](OCC)(OCC)OCC.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)C>CCOC(C)=O.C(OCC)C>[C:28]1([N:27]2[C:13](=[O:15])[C:3]3[S:4][CH:5]=[C:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:2]=3[N:1]=[CH:17]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 31214Ethyl orthoformateHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylate

Product 1

HCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-oneYield 33%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

Methyl 3-amino-4-phenylthiophene-2-carboxylate (100 mg, 0.43 mmol), triethyl orthoformate (1 ml), aniline (76 mg, 0.81 mmol), and acetic acid (0.1 ml) were placed in a pressure bottle. The mixture was heated with stirring at 160° C. for 18 hr. After the completion of the reaction was confirmed by TLC, the reaction mixture was cooled to room temperature and solidified with diethyl ether and EtOAc to give 42 mg (0.14 mmol, 33% yield) of the title compound as a final product.

Workup

  1. temperatureThe mixture was heated
  2. temperaturethe reaction mixture was cooled to room temperature

Sources & evidence

ORD record
ord-63a60616c20242b684ed58d8512b06f3
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Linked notes

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