1-(2-Methoxyphenyl)piperazine → 5-[4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamine

HRID 2294042Notes

Reaction equation

HRID 2294042 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C.Br.Br.Br[CH2:25][C:26]1[C:27]([NH2:33])=[N:28][C:29]([NH2:32])=[N:30][CH:31]=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:25][C:26]2[C:27]([NH2:33])=[N:28][C:29]([NH2:32])=[N:30][CH:31]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 8471TriethylamineHCID 214736085-(Bromomethyl)pyrimidine-2,4-diamine dihydrobromide

Product 1

HCID 214736235-[4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamineYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.2 g (0.017 mol) of 1-(2-methoxy-phenyl)-piperazine in 100 ml of tetrahydrofuran was treated with 11.6 ml (0.084 mol) of triethylamine and 6.1 g (0.017 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. 2.0 g (38%) of 5-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamine were obtained as white crystals; m.p. 195°-196°.

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-404fb7722fae4ab8bb4f3f2f95206a85
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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