2,6-Dimethoxy-4-aminopyrimidine → N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-2-methylbenzenesulfonamide

HRID 27342

Reaction equation

HRID 27342 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([N:22]=[C:23]=[O:24])(=[O:21])=[O:20]>C(Cl)Cl>[CH3:11][O:10][C:4]1[N:3]=[C:2]([NH:1][C:23]([NH:22][S:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH3:12])(=[O:21])=[O:20])=[O:24])[CH:7]=[C:6]([O:8][CH3:9])[N:5]=1

Participants

4

Reactant 2

HCID 767892,6-Dimethoxy-4-aminopyrimidineHCID 2733313o-Toluenesulfonyl Isocyanate

Product 1

HCID 23342477N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-2-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2.40 g of 4-amino-2,6-dimethoxypyrimidine in 40 ml methylene chloride at ambient temperature and pressure was slowly added 3.0 g of 2-methylbenzenesulfonylisocyanate. The reaction was stirred 40 minutes, filtered, and the solid thereby obtained was washed with a small amount of acetonitrile; yield 4.0 g, m.p. 174°-175°, NMR (DMSO-d6) relative to tetramethylsilane: δ 2.77, S, area 30; δ 4.05, S, area 60; δ 6.85, S, area 89; δ 7.7-8.6, multiplets, area 45; δ 10.00, S, area 9.

Workup

  1. filtrationfiltered
  2. customthe solid thereby obtained
  3. washwas washed with a small amount of acetonitrile

Sources & evidence

ORD record
ord-f3ed94953db04dcfa87506272299f2c5
Source dataset
uspto-grants-1980_09
Patent number
US04221585

Linked notes

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