Methylamine → HCID 17774523, compound

HRID 1585708Notes

Reaction equation

HRID 1585708 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:6]=[C:5](Cl)[N:4]=1.[CH3:20][NH2:21]>C1COCC1.[OH-].[Na+]>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:6]=[C:5]([NH:21][CH3:20])[N:4]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 17774521HCID 17774521, compound

Product 1

HCID 17774523HCID 17774523, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
130 °C

Procedure

0.25 g (0.00084 mol) of N-(2-methylamino-6-chloro-pyrimidin-4-yl)-benzenesulfonamide was dissolved in 20 ml of 2M methylamine in THF and stirred in an autoclave at 130° C. for 3 hours. The mixture was freed from solvent, the residue was dissolved in 25 ml of 2N NaOH, filtered and the pH value of the filtrate was adjusted to 6 with 1N HCl. The precipitate was filtered off under suction, dried and chromatographed on silica gel with dichloromethane/methanol 95:5. There was obtained 0.09 g (36%) of N-(2,6-bis-methylamino-pyrimidin-4-yl)-benzenesulfonamide as yellowish crystals; m.p.: >260° C. (dec).

Workup

  1. filtrationfiltered
  2. filtrationThe precipitate was filtered off under suction
  3. customdried
  4. customchromatographed on silica gel with dichloromethane/methanol 95:5

Sources & evidence

ORD record
ord-99ae734656654b4fbf7670518f53bfba
Source dataset
uspto-grants-1999_08
Patent number
US05939451

Reaction notes

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