Triethylamine → 2-Methyl-5-(4-phenethyl-piperazin-1-ylmethyl)-pyrimidin-4-ylamine

HRID 2294026Notes

Reaction equation

HRID 2294026 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.[CH2:12]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:10][C:7]1[N:6]=[C:5]([NH2:11])[C:4]([CH2:3][N:23]2[CH2:24][CH2:25][N:20]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:21][CH2:22]2)=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 792141-PhenethylpiperazineHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)

Product 1

HCID 214736142-Methyl-5-(4-phenethyl-piperazin-1-ylmethyl)-pyrimidin-4-ylamineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.30 g (0.0019 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 20 ml of dimethylformamide was treated with 0.30 g (0.00157 mol) of 1-phenethyl-piperazine and 0.66 ml (0.0047 mol) of triethylamine and the mixture was stirred at room temperature under argon for 36 hours. The mixture was completely freed from the solvents. The residue was partitioned between dichloromethane and water, extracted, chromatographed over silica gel with methanol as the eluent and recrystallized from toluene. 0.39 g (83%) of 2-methyl-5-(4-phenethyl-piperazin-1-ylmethyl)-pyrimidin-4-ylamine was obtained as white crystals; m.p. 162°-165°.

Workup

  1. customThe residue was partitioned between dichloromethane and water
  2. extractionextracted
  3. customchromatographed over silica gel with methanol as the eluent
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-0782c0c1511c480bbfd00c3685b66925
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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