m-Chloroperbenzoic acid → 2-Methanesulfinyl-4'-methyl-[4,5']bipyrimidinyl-2'-ylamine

HRID 1397166Notes

Reaction equation

HRID 1397166 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=2)=[CH:6][N:5]=[C:4]([NH2:16])[N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:25])C=1>C(Cl)Cl.O>[CH3:15][S:14]([C:10]1[N:9]=[C:8]([C:7]2[C:2]([CH3:1])=[N:3][C:4]([NH2:16])=[N:5][CH:6]=2)[CH:13]=[CH:12][N:11]=1)=[O:25]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 679838664'-Methyl-2-methylsulfanyl-[4,5']bipyrimidinyl-2'-ylamine

Product 1

HCID 679833892-Methanesulfinyl-4'-methyl-[4,5']bipyrimidinyl-2'-ylamineYield 17.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4′-Methyl-2-methylsulfanyl-[4,5]bipyrimidinyl-2′-ylamine (19) (380 mg, 1.629 mmol) in DCM (3.258 mL) was added mCPBA (402 mg, 1.629 mmol). The reaction turned to a brown solution, and immediately the reaction was complete. The reaction mixture was diluted with DCM and water. The organic layer was washed with saturated sodium bicarbonate and brine, dried with sodium sulfate, and concentrated. The crude residue was purified by flash chromatography with a gradient of 2-10% MeOH in DCM to give the desired product (70 mg, 17%). MS (ES+): m/z=250.1 (100) [MH+]. HPLC: tR=0.64 minute over 3 minutes.

Workup

  1. washThe organic layer was washed with saturated sodium bicarbonate and brine
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography with a gradient of 2-10% MeOH in DCM

Sources & evidence

ORD record
ord-cd319a76c8844357a6ef9218ea54f47b
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

Loading…