Triethylamine → 2-Methyl-5-[4-(2-nitro-phenyl)-piperazin-1-ylmethyl]-pyrimidin-4-ylamine

HRID 2294002

Reaction equation

HRID 2294002 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([O-:3])=[O:2].C(N(CC)CC)C.Cl.Cl[CH2:25][C:26]1[C:27]([NH2:33])=[N:28][C:29]([CH3:32])=[N:30][CH:31]=1>CN(C)C=O>[CH3:32][C:29]1[N:28]=[C:27]([NH2:33])[C:26]([CH2:25][N:13]2[CH2:12][CH2:11][N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[CH2:15][CH2:14]2)=[CH:31][N:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1009491-(2-Nitrophenyl)piperazineHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)

Product 1

HCID 214736622-Methyl-5-[4-(2-nitro-phenyl)-piperazin-1-ylmethyl]-pyrimidin-4-ylamineYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.25 g (0.0060 mol) of 1-(2-nitro-phenyl)-piperazine and 2.1 ml (0.015 mol) of triethylamine in 20 ml of dimethylformamide was treated with 0.97 g (0.0050 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride and the mixture was stirred at room temperature under argon for 3 hours. The mixture was completely freed from the solvents and the residue was triturated in 20 ml of water. The resulting crystals were filtered off under suction, dried and chromatographed over silica gel with dichloromethane/methanol 19:1 as the eluent. 1.25 g (76%) of 2-methyl-5- [4-(2-nitro-phenyl )-piperazin-1-ylmethyl]-pyrimidin-4-ylamine were obtained as a yellow solid.

Workup

  1. customthe residue was triturated in 20 ml of water
  2. filtrationThe resulting crystals were filtered off under suction
  3. customdried
  4. customchromatographed over silica gel with dichloromethane/methanol 19:1 as the eluent

Sources & evidence

ORD record
ord-fa14a891f71440eda38d04d4f8f6b9a3
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Linked notes

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