2-[4-(5-Bromo-2-methoxybenzyl)-1-piperazinyl]pyrimidine → 4-Phenyl-2-[(4-(2-pyrimidinyl)-piperazinyl)methyl]anisole

HRID 234117Notes

Reaction equation

HRID 234117 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[CH2:9][CH2:8]1.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]1([C:18]2[CH:17]=[CH:16][C:15]([O:21][CH3:22])=[C:14]([CH2:13][N:10]3[CH2:11][CH2:12][N:7]([C:2]4[N:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:8][CH2:9]3)[CH:19]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 12403032-[4-(5-Bromo-2-methoxybenzyl)-1-piperazinyl]pyrimidineHCID 178418255HCID 178418255, compound

Product 1

HCID 98457214-Phenyl-2-[(4-(2-pyrimidinyl)-piperazinyl)methyl]anisole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 182 mg 2-[(4-(2-pyrimidinyl)-piperazinyl)methyl]-4- bromoanisole in 1 mL of tetrahydrofuran heated to 60° C. and 6 mg of Pd(PPh3)4 was added. To this mixture 0.5 mL of a 1M solution of phenylmagnesium bromide in tetrahydrofuran was added dropwise. The reaction mixture was heated at relux temperature under nitrogen for 1 hr, cooled to room temperature and the solvent removed by evaporation under reduced pressure to yield 4-phenyl-2-[(4-(2-pyrimidinyl)-piperazinyl)methyl]anisole which was purified by chromatography on silica gel using 5% methanol in dichloromethane as eluent. Evaporation of the solvent yielded 140 mg of a solid which was treated with ethyl acetate-HCl to give 50 mg of 4-phenyl-2-[(4-(2-pyrimidinyl)piperazinyl)methyl]anisole dihydrochloride (Compound 1 ), mp 205°-207° C.

Workup

  1. temperatureThe reaction mixture was heated at relux temperature under nitrogen for 1 hr
  2. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4919be748fa34c228f15b152956edf7a
Source dataset
uspto-grants-1997_01
Patent number
US05594141

Reaction notes

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