Ethylamine → 4-amino-N-(6-ethylamino-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide

HRID 378266Notes

Reaction equation

HRID 378266 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH:19][CH3:20])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:21]([NH2:23])[CH3:22]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([NH:23][CH2:21][CH3:22])[N:15]=[C:14]([NH:19][CH3:20])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 108527114-amino-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide

Product 1

HCID 108532774-amino-N-(6-ethylamino-2-methylamino-pyrimidin-4-yl)-benzenesulfonamideYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.314 g (0.001 mol) of 4-amino-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide and 6.6 ml (0.1 mol) of ethylamine were stirred in 15 ml of ethanol in an autoclave at 130° C. for 3 hours. The reaction mixture was freed from solvent, the residue was suspended in 8 ml of ethanol and treated in an ultra-sound bath for 15 minutes. The precipitate was filtered off, dissolved in 10 ml of 0.1N NaOH and filtered. The filtrate was adjusted to pH 6 with 01N HCl. The precipitate was filtered off under suction, washed with water and dried. There was obtained 0.18 g (56%) of 4-amino-N-(6-ethylamino-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide as white crystals; m.p.: 252° C. (dec.).

Workup

  1. additiontreated in an ultra-sound bath for 15 minutes
  2. filtrationThe precipitate was filtered off
  3. dissolutiondissolved in 10 ml of 0.1N NaOH
  4. filtrationfiltered
  5. filtrationThe precipitate was filtered off under suction
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-3d86680f96b441e0a962cb5deb85622f
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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