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

HRID 1912176Notes

Reaction equation

HRID 1912176 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-cb81425bb85548e4a625b8a5260aec7f
Source dataset
uspto-grants-2013_12
Patent number
US08604042B2

Reaction notes

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