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Acetone → 1-butyl-2,2-dimethyl-6-(pyridin-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2363954
Notes
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Reaction equation

HRID 2363954 reaction equation
[CH2:1]([NH:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[C:17]([NH2:19])=[O:18])[CH2:2][CH2:3][CH3:4].[CH3:20][C:21]([CH3:23])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:1]([N:5]1[C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[S:8][C:7]=2[C:17](=[O:18])[NH:19][C:21]1([CH3:23])[CH3:20])[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 667440183-(Butylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 667429331-butyl-2,2-dimethyl-6-(pyridin-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(butylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (0.100 g, 0.400 mmol), acetone (3.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred for 3 days at 70° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (100 mL). Extraction with ethyl acetate-tetrahydrofuran (2:1, 100 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. The oil was purified by column chromatography (Combiflash, 12 g silica gel, hexane to ethyl acetate) to afford the title compound (0.0879 g, 70%) as a yellow solid:

Workup

  1. extractionExtraction with ethyl acetate-tetrahydrofuran (2:1, 100 mL)
  2. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  3. customgave an oil
  4. customThe oil was purified by column chromatography (Combiflash, 12 g silica gel, hexane to ethyl acetate)

Sources & evidence

ORD record
ord-ec5af06b162d40fb9ff780e0421157c7
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