Aniline → HCID 23071560, compound

HRID 905701Notes

Reaction equation

HRID 905701 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:1]([NH:8][C:9]1[C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=[C:11]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 23071595HCID 23071595, compound

Product 1

HCID 23071560HCID 23071560, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A 1 ml portion of THF solution containing 7.9 mg of 4-benzylamino-2-chloropyrimidine-5-carboxamide and 3.7 mg of aniline, followed by stirring at 90° C. for 20 hours, which was then mixed with 60 mg of PS-tosyl chloride (mfd. by Argonaut Technologies, 2.44 mmol/g), followed by stirring at room temperature for 3 hours. The reaction mixture was mixed with 2 ml of saturated sodium bicarbonate aqueous solution and extracted with 2 ml of chloroform. By evaporating the solvent under a reduced pressure, 6.6 mg of 4-benzylamino-2-phenylaminopyrimidine-5-carboxamide was obtained.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. extractionextracted with 2 ml of chloroform
  3. customBy evaporating the solvent under a reduced pressure

Sources & evidence

ORD record
ord-b7c1d490effd469e8bd371a67d88d9c5
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

Loading…