Dimethyl Sulfone → 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one

HRID 718314Notes

Reaction equation

HRID 718314 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7](OCC)=[O:8].Cl.Cl[C:21]([NH2:23])=[NH:22].CS(C)(=O)=O.[OH-].[NH4+]>O>[NH2:22][C:21]1[NH:23][C:7](=[O:8])[C:6]2[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[S:3][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 6213Dimethyl SulfoneHCID 14923Ammonium HydroxideHCID 3084509Chloroformamidinium chlorideHCID 21529229Ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate

Product 1

HCID 509416622-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate (0.3 g, 1.13 mmol), chloroformamidine hydrochloride (0.33 g, 2.83 mmol) and dimethylsulfone (0.53 g, 5.65 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 (0.28 g, 95%).

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-7c3cfd1039e347a886d8d0e476a34e8f
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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