Cyclopentanone → 6'-(pyridin-4-yl)-1'H-spiro[cyclopentane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2363924Notes

Reaction equation

HRID 2363924 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].O.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20](S(O)(=O)=O)=CC=1.C1(=O)CCCC1>C1(C)C=CC=CC=1>[N:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:13](=[O:14])[NH:15][C:20]4([CH2:21][CH2:22][CH2:17][CH2:27]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 667440746'-(pyridin-4-yl)-1'H-spiro[cyclopentane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-oneYield 186.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (150 mg, 0.68 mmol), p-toluenesulfonic acid monohydrate (50 mg) and cyclopentan-1-one (10 ml) in toluene (20 ml) was heated to reflux overnight. After removal of the solvent, the residue was purified by column chromatography on silica gel (MeOH: dichloromethane=1:9) to afford the title compound (140 mg, yield 72%) as an orange solid:

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customAfter removal of the solvent
  4. customthe residue was purified by column chromatography on silica gel (MeOH: dichloromethane=1:9)

Sources & evidence

ORD record
ord-d6bab68b7b014550b740617eaef21018
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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