Potassium Carbonate → 4-(4-Methyl-piperazin-1-yl)-2-phenyl-pyrimidine

HRID 910691Notes

Reaction equation

HRID 910691 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>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.C1(C)C=CC=CC=1.CCO>[CH3:14][N:11]1[CH2:12][CH2:13][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:7]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 17142252-Chloro-4-(4-methylpiperazin-1-yl)pyrimidine

Product 1

HCID 576131944-(4-Methyl-piperazin-1-yl)-2-phenyl-pyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
140 °C

Procedure

To a microwave tube was added 2-chloro-4-(4-methyl-piperazin-1-yl)-pyrimidine (30 mg, 0.14 mmol), Pd(PPh3)4 (10 mg), phenylboronic acid (24 mg, 0.2 mmol), toluene/EtOH (4:1, 1 mL) and 2 M aqueous K2CO3 (0.2 mL). The resulting mixture was heated at 140° C. for 30 minutes using the microwave instrument. The resulting mixture was extracted with EtOAc. The organic layer was dried and concentrated, and the residue was purified by preparative TLC (hexanes/EtOAc) to yield the title compound as a solid.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe residue was purified by preparative TLC (hexanes/EtOAc)

Sources & evidence

ORD record
ord-8146377012cc4b809b7a9acba3452ec6
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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