2,6-Dimethyl-4-aminopyrimidine → HCID 13176760, compound

HRID 280811

Reaction equation

HRID 280811 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 13176760HCID 13176760, compound

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-5735051ee7314864b53c38f2ea089f2f
Source dataset
uspto-grants-1986_05
Patent number
US04591378

Linked notes

Loading…