Ethyl orthoformate → 3-(3-Methylcyclohexyl)-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1775689Notes

Reaction equation

HRID 1775689 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]1C(C2C=CC=CC=2)=CSC=1C(OC)=O.C(OCC)(OCC)OCC.CC1CCCC(N)C1>C(O)(=O)C>[CH3:24][CH:3]1[CH2:4][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]1

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 1109313-Methylcyclohexylamine, mixed isomersHCID 2759782Methyl 3-amino-4-phenylthiophene-2-carboxylateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 783236463-(3-Methylcyclohexyl)-7-phenylthieno[3,2-d]pyrimidin-4(3H)-oneYield 70.5%

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), 3-methylcyclohexanamine (0.120 ml, 0.90 mmol), and acetic acid (0.1 ml) were used to give 98.4 mg (0.30 mmol, 70.5% yield) of the title compound.

Sources & evidence

ORD record
ord-d95b060a3a4c434ab3ea5bc0f75e301a
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

Loading…