4-Chloroaniline → N-(4-chlorophenyl)-4-(pyrimidin-4-ylmethyl)phthalazin-1-amine

HRID 1384142Notes

Reaction equation

HRID 1384142 reaction equation
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][N:15]=2)=[N:5][N:4]=1.[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>ClCCl.CO>[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]([CH2:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][N:15]=3)=[N:5][N:4]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 227419711-Chloro-4-(4-pyrimidinylmethyl)phthalazine hydrochloride

Product 1

HCID 6326418N-(4-chlorophenyl)-4-(pyrimidin-4-ylmethyl)phthalazin-1-amine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 100 mg (0.45 mmol) 1-chloro-4-(4-pyrimidinylmethyl)phthalazine hydrochloride and 149 mg (1.17 mmol) 4-chloroaniline is heated for 1.5 h to 100° C. The reaction mixture is distributed between dichloromethane/CH3OH 19:1 and sat. NaHCO3solution. The organic phase is separated off, washed with water and brine, dried (Na2SO4), and concentrated by evaporation. Chromatography (SiO2; ethyl acetate/CH3OH 19:1) and crystallization from ethyl acetate/ether yield the title compound: m.p.: 174-176° C.; FAB MS (M+H)+=348.

Workup

  1. temperatureis heated for 1.5 h to 100° C
  2. customThe organic phase is separated off
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation
  6. customChromatography (SiO2; ethyl acetate/CH3OH 19:1) and crystallization from ethyl acetate/ether

Sources & evidence

ORD record
ord-c4ac3d1e32664a8fac12767b05efd4ee
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

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