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

HRID 1170730Notes

Reaction equation

HRID 1170730 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-d67393a4471a4d3f9b74a49a990d975c
Source dataset
uspto-grants-2010_11
Patent number
US07825246B2

Reaction notes

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