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

HRID 2363923Notes

Reaction equation

HRID 2363923 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(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1.CC(C)=O>C1(C)C=CC=CC=1>[CH3:18][C:17]1([CH3:22])[NH:1][C:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=3)[S:4][C:3]=2[C:13](=[O:14])[NH:15]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 667437712,2-dimethyl-6-(pyridin-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneYield 190.7%

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 acetone (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 (130 mg, yield 74%) 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-a65f3ce853fb4c5b8929be8ff48f5166
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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