1-Phenylpiperazine → 5-(4-Phenyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamine

HRID 2294032Notes

Reaction equation

HRID 2294032 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br.Br.Br[CH2:23][C:24]1[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=1>O1CCCC1>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:23][C:24]3[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 214736085-(Bromomethyl)pyrimidine-2,4-diamine dihydrobromide

Product 1

HCID 214736725-(4-Phenyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamineYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.14 g (0.00086 mol) of 1-phenyl-piperazine in 10 ml of tetrahydrofuran was treated with 0.6 ml (0.0043 mol) of triethylamine and 0.24 g (0.00086 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. 0.14 g (57%) of 5-(4-phenyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamine was obtained as white crystals; m.p. 263°-265°. A further 0.04 g of yellowish crystals was recovered from the mother liquor.

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-be4176dd37174086b95cef00aec5ab70
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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