4-(4-Methylpiperazin-1-yl)aniline → 5-Methyl-N~2~-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidine-2,4-diamine

HRID 491195Notes

Reaction equation

HRID 491195 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1>C(O)(=O)C>[CH3:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([N:14]3[CH2:13][CH2:12][N:11]([CH3:10])[CH2:16][CH2:15]3)=[CH:22][CH:21]=2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 43021752-Chloro-5-methylpyrimidin-4-amine

Product 1

HCID 569241695-Methyl-N~2~-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (1.0 g, 6.9 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (1.5 mL, 7.8 mmol) in acetic acid (15 mL) was heated at 100° C. for 2.5 h. The mixture was allowed to cool to room temperature and acetic acid removed under reduced pressure. The residue was taken in water (20 mL) and the mixture was neutralized with 10% NaOH solution until solid precipitated. After filtration and washed with water, the title compound was obtained as a grey solid (1.3 g, 63%).

Workup

  1. temperatureto cool to room temperature
  2. customacetic acid removed under reduced pressure
  3. customprecipitated
  4. filtrationAfter filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-d186423187d5408a94a62e4dd57fed0f
Source dataset
uspto-grants-2009_05
Patent number
US07528143B2

Reaction notes

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