2-Methylpyrimidin-4-amine → 3-chloro-2-methyl-N-(2-methyl-pyrimidin-4-yl)-benzenesulfonamide

HRID 1786123Notes

Reaction equation

HRID 1786123 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[C:11]([CH3:20])=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1>N1C=CC=CC=1>[Cl:9][C:10]1[C:11]([CH3:20])=[C:12]([S:16]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=2)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 2957632-Methylpyrimidin-4-amineHCID 5227343-Chloro-2-methylbenzenesulfonyl chloride

Product 1

HCID 115511263-chloro-2-methyl-N-(2-methyl-pyrimidin-4-yl)-benzenesulfonamideYield 9.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
55 °C

Procedure

2-Methyl-pyrimidin-4-ylamine (91 mg, Gabriel, Chem. Ber. 37, 1904, 3641) and 3-chloro-2-methyl-benzenesulfonyl chloride (179 mg) were dissolved in pyridine (5 mL) and the resulting mixture was allowed to stir at 50 to 60° C. for 48 hours. The mixture was then evaporated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with 1M CuSO4 solution twice, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (CH2Cl2MeOH/NH3 90:10:0.5) to give the desired product 3-chloro-2-methyl-N-(2-methyl-pyrimidin-4-yl)-benzenesulfonamide as a yellow powder (22 mg). MS (ESI−): 297.1 ([M−H]−).

Workup

  1. customThe mixture was then evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 1M CuSO4 solution twice
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (CH2Cl2MeOH/NH3 90:10:0.5)

Sources & evidence

ORD record
ord-acaf3c8ea1a74418ae4033db058a9924
Source dataset
uspto-grants-2009_03
Patent number
US07507733B2

Reaction notes

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