Dimethyl Sulfone → 2-Aminothieno[2,3-d]pyrimidin-4(3H)-one

HRID 1396783Notes

Reaction equation

HRID 1396783 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]CC)=O.Cl.Cl[C:14]([NH2:16])=[NH:15].CS(C)(=O)=O.[OH-].[NH4+]>O>[NH2:15][C:14]1[NH:16][C:7](=[O:9])[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 6213Dimethyl SulfoneHCID 14923Ammonium HydroxideHCID 1988156Ethyl 2-aminothiophene-3-carboxylateHCID 3084509Chloroformamidinium chloride

Product 1

HCID 667583302-Aminothieno[2,3-d]pyrimidin-4(3H)-oneYield 45.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of ethyl 2-aminothiophene-3-carboxylate (0.5 g, 3.18 mmol), chloroformamidine hydrochloride (0.91 g, 7.95 mmol) and dimethylsulfone (1.50 g, 15.9 mmol) was heated at 120-130° C. for 30 minutes. After cooling down to room temperature, water (10 ml) was added and ammonium hydroxide was used to neutralize the suspension. The solid was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 10:1) to yield the title compound as a white solid (0.24 g, 45%).

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. customdried
  5. customThe crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 10:1)

Sources & evidence

ORD record
ord-15c186d561b34ccabadc1cbaa16eecaf
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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