Methane → N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide

HRID 463620Notes

Reaction equation

HRID 463620 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:2]=1.C[Al](C)C.C.[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH:24][C:25](=O)[O:26]C)[N:18]=1>C(Cl)Cl.C(O)(=O)C>[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH:24][C:25]([NH:10][S:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:9])=[O:8])=[O:26])[N:18]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 232710pyridine-3-sulfonamideHCID 13278970Methyl (4,6-dimethylpyrimidin-2-yl)carbamateHCID 16682925Trimethylaluminum

Product 1

HCID 13533294N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 3-pyridinesulfonamide (1 m mole) in methylene chloride is added 2 m mole of trimethylaluminum. Following methane evolution, the reaction mixture becomes homogeneous, whereupon 1 m mole of methyl (4,6-dimethylpyrimidin-2-yl)carbamate is added, and stirring is continued for 66 hours. Aqueous acetic acid is added and the product is extracted into methylene chloride. The solvent is evaporated and the product is isolated by trituration on chromatography.

Workup

  1. additionis added
  2. extractionthe product is extracted into methylene chloride
  3. customThe solvent is evaporated
  4. customthe product is isolated by trituration on chromatography

Sources & evidence

ORD record
ord-4aa4af493cc943bd9a2c9a0cd82aa833
Source dataset
uspto-grants-1985_10
Patent number
US04544401

Reaction notes

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