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

HRID 1507873Notes

Reaction equation

HRID 1507873 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 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of ethyl 2-amino-thiophene-3-carboxylate (0.4 g, 2.34 mmol), chloroformamidine hydrochloride (0.67 g, 5.84 mmol) and dimethylsulfone (0.53 g, 11.7 mmol) was heated at 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 till pH=8. The solid was filtered off, washed with water and dried, yielding the crude title compound (71%, 277 mg). The crude residue was used as such for further reaction.

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2c93be26a930496bb9804937710d3444
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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