2,5-Dimethylaniline → HCID 78320482, compound

HRID 1775622Notes

Reaction equation

HRID 1775622 reaction equation
C1(N2[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)C=CC=CC=1.NC1C(C2C=CC=CC=2)=CSC=1C(OC)=O.C(OCC)(OCC)OCC.[CH3:49][C:50]1[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][C:51]=1[NH2:52]>C(O)(=O)C>[CH3:49][C:50]1[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][C:51]=1[N:52]1[C:12](=[O:13])[C:11]2[S:14][CH:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[N:9]=[CH:8]1

Participants

6

Reactant 4

HCID 72592,5-DimethylanilineHCID 31214Ethyl orthoformateHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78320482HCID 78320482, compoundYield 44%

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 (45.6 mg, 0.20 mmol), triethyl orthoformate (0.40 ml), 2,5-dimethylaniline (44.8 mg, 0.37 mmol), and acetic acid (0.05 ml) were used to give 28.8 mg (0.087 mmol, 44% yield) of the title compound.

Sources & evidence

ORD record
ord-4c5d2a6832324f048453e53fea1e320a
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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