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

HRID 2363962
Notes
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Reaction equation

HRID 2363962 reaction equation
[CH2:1]([NH:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([NH2:17])=[O:16])[CH3:2].[C:18]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:1]([N:3]1[C:4]2[CH:8]=[C:7]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)[S:6][C:5]=2[C:15](=[O:16])[NH:17][C:18]21[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 667438263-(Ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 468982461'-ethyl-6'-(pyridin-4-yl)-1'H-spiro [cyclopentane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-oneYield 28%

Reagents, catalysts & solvents

1
HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (0.100 g, 0.400 mmol), cyclopentanone (2.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred for 2 h at 100° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate (100 mL, 50 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. This oil was purified by column chromatography (Combiflash, 40 g silica gel, dichloromethane to ethyl acetate), then triturated with ethyl acetate, and the precipitate was collected by filtration to afford the title compound (0.0434 g, 28%) as a yellow solid:

Workup

  1. extractionExtraction with ethyl acetate (100 mL, 50 mL)
  2. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  3. customgave an oil
  4. customThis oil was purified by column chromatography (Combiflash, 40 g silica gel, dichloromethane to ethyl acetate)
  5. customtriturated with ethyl acetate
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-f48b2b30247e4b719b377904ce302135
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691828B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes