Triethylamine → 5-[4-(2-Chloro-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamine

HRID 2294041Notes

Reaction equation

HRID 2294041 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C.Br.Br.Br[CH2:24][C:25]1[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:24][C:25]2[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4156281-(2-Chlorophenyl)piperazineHCID 214736085-(Bromomethyl)pyrimidine-2,4-diamine dihydrobromide

Product 1

HCID 214736535-[4-(2-Chloro-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamineYield 55.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.0 g (0.031 mol) of 1-(2-chloro-phenyl)-piperazine in 300 ml of tetrahydrofuran was treated with 22 ml (0.16 mol) of triethylamine and 11.5 g (0.031 mol) of 5-bromomethyl-pyrimidine-2,4-diamine dihydrobromide and the mixture was stirred at room temperature under argon for 16 hours. The suspension obtained was suction filtered and the filtrate was completely freed from the solvents. The residue was chromatographed over silica gel with acetonitrile/methanol 1:1 as the eluent and digested in diethyl ether. 5.5 g (55%) of 5-[4-(2-chloro-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamine were obtained as beige crystals; m.p. 2:30°-235°.

Workup

  1. customThe suspension obtained
  2. filtrationfiltered
  3. customThe residue was chromatographed over silica gel with acetonitrile/methanol 1:1 as the eluent and digested in diethyl ether

Sources & evidence

ORD record
ord-80465b86ee504655958d9d1df06daa62
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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