Dimethyl Sulfoxide → HCID 90111505, compound

HRID 1509044Notes

Reaction equation

HRID 1509044 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11](OS(C(F)(F)F)(=O)=O)[C:10]([CH2:21][CH3:22])=[C:9]([CH3:23])[N:8]=2)=[CH:4][CH:3]=1.[CH3:24][C:25]1([CH3:39])[C:29]([CH3:31])([CH3:30])[O:28][B:27]([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[O:26]1.CS(C)=O>O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:12]=[C:11]([NH:36][C:35]3[CH:34]=[CH:33][C:32]([B:27]4[O:28][C:29]([CH3:31])([CH3:30])[C:25]([CH3:39])([CH3:24])[O:26]4)=[CH:38][CH:37]=3)[C:10]([CH2:21][CH3:22])=[C:9]([CH3:23])[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 90110220HCID 90110220, compound

Product 1

HCID 90111505HCID 90111505, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 18-mL vial was charged with [2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]trifluoromethanesulfonate (39 mg, 0.1 mmole) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (22 mg, 0.1 mmol) and DMSO (0.5 ml). The resulting mixture was stirred under Ar for 3.5 hr. After cooling to room temperature, water was added to the mixture (5 ml). The precipitate was collected by filtration and the crude product was purified by chromatography on silica gel using hexane/DCM (4:1) followed by 2% of methanol in DCM as eluent to afford the title compound, containing impurities, which was forward to the next step without any further purification (10.3 mg, 23% yield).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2b1a8d1d48a8492aadda927bbdcc97eb
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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