3,4-Dimethylaniline → HCID 78320483, compound

HRID 1775623Notes

Reaction equation

HRID 1775623 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:51]=[C:52]([CH:54]=[CH:55][C:56]=1[CH3:57])[NH2:53]>C(O)(=O)C>[CH3:49][C:50]1[CH:51]=[C:52]([N:53]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:54]=[CH:55][C:56]=1[CH3:57]

Participants

6

Reactant 4

HCID 72483,4-DimethylanilineHCID 31214Ethyl orthoformateHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78320483HCID 78320483, compoundYield 50%

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 (70 mg, 0.30 mmol), triethyl orthoformate (0.57 ml), 3,4-dimethylaniline (67.8 mg, 0.56 mmol), and acetic acid (0.07 ml) were used to give 49.2 mg (0.15 mmol, 50% yield) of the title compound.

Sources & evidence

ORD record
ord-bc8aee14ca774e89b4c6950b1b0c31ce
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

Loading…