Ethyl orthoformate → HCID 78323321, compound

HRID 1775683Notes

Reaction equation

HRID 1775683 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)C=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C(C2C=CC=CC=2)=CSC=1C(OC)=[O:36].C(OCC)(OCC)OCC.O1CCC[C@H]1CN>C(O)(=O)C>[C:17]1([C:16]2[C:10]3[N:9]=[CH:8][N:7]([CH2:1][C@@H:2]4[CH2:3][CH2:4][CH2:5][O:36]4)[C:12](=[O:13])[C:11]=3[S:14][CH:15]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 641530(S)-(+)-TetrahydrofurfurylamineHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 78323321HCID 78323321, compoundYield 67.1%

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), (S)-(tetrahydrofuran-2-yl)methanamine (0.102 ml, 0.99 mmol), and acetic acid (0.1 ml) were used to give 90.1 mg (0.29 mmol, 67.1% yield) of the title compound.

Sources & evidence

ORD record
ord-c08f6a942a2c4046976ac0e37f74881b
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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