2,6-Dimethylaniline → HCID 78320480, compound

HRID 1775621Notes

Reaction equation

HRID 1775621 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][CH:54]=[C:53]([CH3:57])[C:51]=1[NH2:52]>C(O)(=O)C>[CH3:49][C:50]1[CH:56]=[CH:55][CH:54]=[C:53]([CH3:57])[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 68962,6-DimethylanilineHCID 31214Ethyl orthoformateHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78320480HCID 78320480, compoundYield 56%

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 (43 mg, 0.18 mmol), triethyl orthoformate (0.34 ml), 2,6-dimethylaniline (0.04 ml, 0.33 mmol), and acetic acid (0.042 ml) were used to give 34.8 mg (0.10 mmol, 56% yield) of the title compound.

Sources & evidence

ORD record
ord-5f62eeecc3a74f1383ad1b4559c7d3a9
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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