2,6-Dimethyl-4-aminopyrimidine → N-[(2,6-dimethylpyrimidin-4-yl)aminocarbonyl]2-methoxycarbonylbenzenesulfonamide

HRID 1074966Notes

Reaction equation

HRID 1074966 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][O:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21])=[O:13]>C(#N)C>[CH3:9][C:4]1[N:3]=[C:2]([NH:1][C:24]([NH:23][S:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:12]([O:11][CH3:10])=[O:13])(=[O:22])=[O:21])=[O:25])[CH:7]=[C:6]([CH3:8])[N:5]=1

Participants

4

Reactant 2

HCID 680392,6-Dimethyl-4-aminopyrimidineHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 13176760N-[(2,6-dimethylpyrimidin-4-yl)aminocarbonyl]2-methoxycarbonylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1.2 g of 4-amino-2,6-dimethylpyrimidine in 30 ml of dry acetonitrile with stirring was added 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate. The mixture was stirred for two hours at ambient temperature, allowed to stand for sixteen hours and the desired product, which had precipitated, was removed by filtration and washed with butyl chloride to yield 2.4 g, m.p. 125°-127°. The product showed absorption peaks by Nuclear Magnetic Resource at 4.0, 2.62 and 2.9 ppm; consistent for the product.

Workup

  1. stirringThe mixture was stirred for two hours at ambient temperature
  2. waitto stand for sixteen hours
  3. customthe desired product, which had precipitated
  4. customwas removed by filtration
  5. washwashed with butyl chloride
  6. customto yield 2.4 g, m.p. 125°-127°
  7. customabsorption peaks by Nuclear Magnetic Resource at 4.0, 2.62 and 2.9 ppm

Sources & evidence

ORD record
ord-11c10d0a954c40588c83983673205a7e
Source dataset
uspto-grants-1983_07
Patent number
US04394506

Reaction notes

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