Ethyl orthoformate → HCID 86729820, compound

HRID 1775703Notes

Reaction equation

HRID 1775703 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.N[C:24]1[C:28]([C:29]2C=CC=CC=2)=[CH:27]SC=1C(OC)=O.C(OCC)(OCC)OCC.C(C1CCC(N)CC1)(C)(C)C>C(O)(=O)C>[C:28]([CH:4]1[CH2:5][CH2:6][CH: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)[CH2:2][CH2:3]1)([CH3:29])([CH3:24])[CH3:27]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 793964-tert-ButylcyclohexylamineHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 86729820HCID 86729820, compoundYield 65.4%

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 ml), 4-t-butylcyclohexylamine (0.161 ml, 0.90 mmol), and acetic acid (0.1 ml) were used to give 103.1 mg (0.28 mmol, 65.4% yield) of the title compound.

Sources & evidence

ORD record
ord-b49104744069435ea73fbd563ca072ba
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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