Acetic Acid → 3-(4-Methoxyphenyl)-2-methyl-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1775668Notes

Reaction equation

HRID 1775668 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][S:4][C:3]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:14].[C:24](OCC)(OCC)(OCC)[CH3:25].C(O)(=O)C.C(OCC)C>CCOC(C)=O>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([N:15]2[C:13](=[O:14])[C:3]3[S:4][CH:5]=[C:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:2]=3[N:1]=[C:24]2[CH3:25])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 66221Triethyl orthoacetateHCID 867298003-Amino-N-(4-methoxyphenyl)-4-phenylthiophene-2-carboxamide

Product 1

HCID 783226943-(4-Methoxyphenyl)-2-methyl-7-phenylthieno[3,2-d]pyrimidin-4(3H)-oneYield 21%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-N-(4-methoxyphenyl)-4-phenylthiophene-2-carboxamide (57 mg, 0.18 mmol), triethyl orthoacetate (1 ml), and acetic acid (0.1 ml) were placed in a pressure bottle. The mixture was heated with stiffing at 160° C. for 18 hr. After the completion of the reaction was confirmed by TLC, the reaction mixture was cooled to room temperature and solidified with diethyl ether and EtOAc to give 13 mg (0.037 mmol, 21% yield) of the title compound.

Workup

  1. temperatureThe mixture was heated

Sources & evidence

ORD record
ord-ce52aa5e3eab4902988d9082d362f262
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

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