m-Chloroperbenzoic acid → N-{2-[4-(2-Methanesulfinyl-pyrimidin-4-ylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

HRID 76179Notes

Reaction equation

HRID 76179 reaction equation
[CH3:1][CH:2]([NH:20][C:21](=[O:23])[CH3:22])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=2)=[CH:6][CH:5]=1.ClC1C=C(C=CC=1)C(OO)=[O:29].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:19][S:18]([C:14]1[N:13]=[C:12]([C:11]#[C:10][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][CH:2]([NH:20][C:21](=[O:23])[CH3:22])[CH3:1])=[CH:9][CH:8]=2)[CH:17]=[CH:16][N:15]=1)=[O:29]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66611369N-{1-Methyl-2-[4-(2-methylsulfanyl-pyrimidin-4-ylethynyl)-phenyl]-ethyl}acetamide

Product 1

HCID 66614281N-{2-[4-(2-Methanesulfinyl-pyrimidin-4-ylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 0.30 g (0.922 mmol) N-{1-methyl-2-[4-(2-methylsulfanyl-pyrimidin-4-ylethynyl)-phenyl]-ethyl}-acetamide (example 14.1) in 9 mL DCM is cooled down to 0° C. and charged with 0.27 g (1.10 mmol; 70% purity) 3-chloroperoxybenzoic acid. The mixture is stirred for 30 min at constant temperature. The mixture is poured onto sat. aq. NaHCO3 solution. The organic layer is separated, dried with Na2SO4 and filtered. The resulting mixture can be used directly used in the following reaction.

Workup

  1. customThe organic layer is separated
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. customThe resulting mixture can be used directly used in the following reaction

Sources & evidence

ORD record
ord-edfcfc2ce2864381b67df2a46129db22
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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