Potassium Carbonate → N-(4-(2-chloropyrimidin-4-yl)phenyl)-N-(cyanomethyl)methanesulfonamide

HRID 589574Notes

Reaction equation

HRID 589574 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]#[N:28]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([N:14]([CH2:26][C:27]#[N:28])[S:15]([CH3:18])(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 44627479HCID 44627479, compound

Product 1

HCID 86706917N-(4-(2-chloropyrimidin-4-yl)phenyl)-N-(cyanomethyl)methanesulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(4-(2-chloropyrimidin-4-yl)phenyl)methanesulfonamide (750 mg 2.64 mmol) and potassium carbonate (730 mg, 2 eq.) were placed in a round bottomed flask and suspended in acetone (50 mL). The mixture was stirred for several minutes before adding bromoacetonitrile (368 μL, 2 eq.). The reaction mixture was stirred at room temperature for 48 h. The crude reaction mixture was concentrated in vacuo and the residue taken up in ethyl acetate (200 mL) and washed with water (2×100 mL), brine (100 mL) and then dried (sodium sulfate). The organic phase was concentrated in vacuo to give N-(4-(2-chloropyrimidin-4-yl)phenyl)-N-(cyanomethyl)methanesulfonamide (762 mg, 89% yield) as a fawn solid. 1H NMR (300 MHz, d6-DMSO) δ 8.86 (1H, d, J=5.0 Hz); 8.28 (2H, d, J=8.7 Hz); 8.18 (1H, d, J=5.5 Hz); 7.66 (2H, d, J=8.7 Hz); 4.97 (2H, s); 3.22 (3H, s). LC-ESI-MS (method B): rt 5.9 min.; m/z 323.2/325.2 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 48 h
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. washwashed with water (2×100 mL), brine (100 mL)
  5. dry with materialdried (sodium sulfate)
  6. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-20140847588d4f22abcade04811074bf
Source dataset
uspto-grants-2016_01
Patent number
US09233934B2

Reaction notes

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