Ethyl orthoformate → HCID 78323002, compound

HRID 1775679Notes

Reaction equation

HRID 1775679 reaction equation
C1([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)C=CC=CC=1.NC1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=CSC=1C(OC)=O.C(OCC)(OCC)OCC.C1(CN)CCCCC1>C(O)(=O)C>[CH:29]1([CH2:28][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)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 76688CyclohexanemethylamineHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78323002HCID 78323002, compoundYield 73.3%

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), cyclohexanemethylamine (0.129 ml, 0.99 mmol), and acetic acid (0.1 ml) were used to give 102.3 mg (0.32 mmol, 73.3% yield) of the title compound.

Sources & evidence

ORD record
ord-63e3043bfdd94e729f5c912e8d0274d0
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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