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

HRID 718317Notes

Reaction equation

HRID 718317 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-a423d7c138d748518fa639d33006809a
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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