3-Fluoroaniline → 3-(3-Fluorophenyl)-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1775606

Reaction equation

HRID 1775606 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C(C2C=CC=CC=2)=CSC=1C(OC)=O.C(OCC)(OCC)OCC.[F:49]C1C=C(C=CC=1)N>C(O)(=O)C>[F:49][C:3]1[CH:2]=[C:1]([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 97423-FluoroanilineHCID 31214Ethyl orthoformateHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 783248673-(3-Fluorophenyl)-7-phenylthieno[3,2-d]pyrimidin-4(3H)-oneYield 12%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-phenylthiophene-2-carboxylate (50 mg, 0.21 mmol), triethyl orthoformate (0.47 ml), 3-fluoroaniline (44.3 mg, 0.4 mmol), and acetic acid (0.06 ml) were used to give 8.1 mg (0.025 mmol, 12% yield) of the title compound.

Sources & evidence

ORD record
ord-171d5fd97a9847699e1dd731638bddc1
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Linked notes

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