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

HRID 2294038Notes

Reaction equation

HRID 2294038 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=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>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:25][C:26]3[C:27]([NH2:33])=[N:28][C:29]([NH2:32])=[N:30][CH:31]=3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2697221-(4-Methoxyphenyl)piperazineHCID 214736085-(Bromomethyl)pyrimidine-2,4-diamine dihydrobromide

Product 1

HCID 214736195-[4-(4-Methoxy-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamineYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.95 g (0.00494 mol) of 1-(4-methoxy-phenyl)-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 65 hours. The mixture was completely freed from the solvents. The residue was chromatographed over silica gel with acetonitrile/methanol (1:1 ), digested in diethyl ether and subsequently filtered off under suction. 0.24 g (47%) of 5-[4-(4-methoxy-phenyl)-piperazin-1-ylmethyl]-pyrimidine-2,4-diamine was obtained as white crystals; m.p. 239°-241°.

Workup

  1. customThe residue was chromatographed over silica gel with acetonitrile/methanol (1:1 )
  2. filtrationsubsequently filtered off under suction

Sources & evidence

ORD record
ord-c97c882a7aa249c09f11774b320d1579
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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