Triethylamine → 5-(4-p-Tolyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamine

HRID 2294036

Reaction equation

HRID 2294036 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=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>CN(C)C=O>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:24][C:25]3[C:26]([NH2:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=3)[CH2:11][CH2:12]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 831131-(p-Tolyl)piperazineHCID 214736085-(Bromomethyl)pyrimidine-2,4-diamine dihydrobromide

Product 1

HCID 214736335-(4-p-Tolyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamineYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.87 g (0.00493 mol) of 1-p-tolyl-piperazine in 30 ml of dimethylformamide was treated with 1.37 ml (0.00986 mol) of triethylamine and 0.60 g (0.00164 mol) of 5-bromomethyl-pyrimidine-2,4-diamine dihydrobromide and the mixture was stirred at room temperature under argon for 110 hours. The mixture was completely freed from the solvents. The residue was chromatographed over silica gel with methanol as the eluent, digested in dichloromethane/water 1:1 and subsequently filtered off under suction. 0.25 g (51%) of 5-(4-p-tolyl-piperazin-1-ylmethyl)-pyrimidine-2,4-diamine was obtained as beige crystals; m.p. 248°-250°.

Workup

  1. customThe residue was chromatographed over silica gel with methanol as the eluent
  2. filtrationsubsequently filtered off under suction

Sources & evidence

ORD record
ord-521d9de644634cf084fe6b6c555047c4
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Linked notes

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