Ethylamine → 4-Amino-N-(2-amino-6-ethylamino-pyrimidin-4-yl)-benzenesufonamide

HRID 378261Notes

Reaction equation

HRID 378261 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]([NH2:19])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:20]([NH2:22])[CH3:21]>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:22][CH2:20][CH3:21])[N:15]=[C:14]([NH2:19])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 107329394-amino-N-(2-amino-6-chloro-pyrimidin-4-yl)-benzenesulfonamide

Product 1

HCID 107335984-Amino-N-(2-amino-6-ethylamino-pyrimidin-4-yl)-benzenesufonamideYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
130 °C

Procedure

0.50 g (0.00167 mol) of 4-amino-N-(2-amino-6-chloropyrimidin-4-yl)-benzenesufonamide and 11 ml (0.167 mol) of ethylamine were dissolved in 20 ml of ethanol and stirred in an autoclave at 130° C. for 4 hours. The reaction mixture was freed from solvent, the residue was suspended in 5 ml of ethanol and treated in an ultrasound bath for 15 minutes. The precipitate was filtered off, dissolved 10 ml of 0.1N NaOH and filtered. The filtrate was adjusted to pH 6 with 0.1N HCl. The precipitate was filtered off under suction, washed with water and dried. There was obtained 0.271 g (53%) of 4-amino-N-(2-amino-6-ethylamino-pyrimidin-4-yl)-benzenesulfonamide as beige crystals; m.p. 272-274° C.

Workup

  1. additiontreated in an ultrasound bath for 15 minutes
  2. filtrationThe precipitate was filtered off
  3. dissolutiondissolved 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-0edc4226fa484de9b7f2dc1416f466e8
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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