Isopropylamine → 4-amino-N-(2-ethylamino-6-isopropylamino-pyrimidin-4-yl)-benzenesulfonamide

HRID 1584185Notes

Reaction equation

HRID 1584185 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][CH2:20][CH3:21])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23]>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:25][CH:22]([CH3:24])[CH3:23])[N:15]=[C:14]([NH:19][CH2:20][CH3:21])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 108300934-amino-N-(6-chloro-2-ethylamino-pyrimidin-4-yl)-benzenesulfonamide

Product 1

HCID 107840674-amino-N-(2-ethylamino-6-isopropylamino-pyrimidin-4-yl)-benzenesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.5 g (0.0015 mol) of 4-amino-N-(6-chloro-2-ethylamino-pyrimidin-4-yl)-benzenesulfonamide was dissolved in 20 ml of ethanol and stirred with 13 ml (0.15 mol) of isopropylamine 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 in 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 0.20 g (37%) of 4-amino-N-(2-ethylamino-6-iso-propylamino-pyrimidin-4-yl)-benzenesulfonamide as white crystals; m.p.: 258-259° C.

Workup

  1. additiontreated in an ultrasound 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-d185d1caed1f4860af78c4436372c014
Source dataset
uspto-grants-1999_08
Patent number
US05932599

Reaction notes

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