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

HRID 485521Notes

Reaction equation

HRID 485521 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 4amino-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-afa5c3f05cc74b818712c1cbbb0f2591
Source dataset
uspto-grants-1985_08
Patent number
US04536576

Reaction notes

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