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

HRID 2359763
Notes
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Reaction equation

HRID 2359763 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-f75c3bb2afe546ce9f50661154052907
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08685993B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes