Ethyl orthoformate → HCID 78323323, compound

HRID 1775687Notes

Reaction equation

HRID 1775687 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.[CH2:49]([NH2:54])[C:50]([CH3:53])([CH3:52])[CH3:51]>C(O)(=O)C>[CH2:49]([N:54]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)[C:50]([CH3:53])([CH3:52])[CH3:51]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 79882NeopentylamineHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78323323HCID 78323323, compoundYield 35.7%

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 (100 mg, 0.43 mmol), triethyl orthoformate (1.0 ml), neopentylamine (0.117 ml, 0.99 mmol), and acetic acid (0.1 ml) were used to give 45.8 mg (0.15 mmol, 35.7% yield) of the title compound.

Sources & evidence

ORD record
ord-0a5736c2b775495189fb273b45eb07a9
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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