2,6-Dichloro-N,N-dimethylpyrimidin-4-amine → HCID 23026702, compound

HRID 1666679Notes

Reaction equation

HRID 1666679 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Cl:5][C:6]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([Cl:15])[N:7]=1>C(OCC)C.C1COCC1.C(Cl)(Cl)Cl.[Br-].[Zn+2].[Br-].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>[Cl:5][C:6]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([CH2:1][CH3:2])[N:7]=1.[Cl:15][C:8]1[N:7]=[C:6]([CH2:1][CH3:2])[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[CH:9]=1

Participants

9

Reactant 2

HCID 154386932,6-Dichloro-N,N-dimethylpyrimidin-4-amineHCID 178418443HCID 178418443, compound

Product 2

HCID 23026702HCID 23026702, compoundHCID 23027070HCID 23027070, compound

Reagents, catalysts & solvents 5

HCID 10421208Zinc bromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-65 °C

Procedure

A mixture of zinc bromide (2.6 g) and THF (15 mL) was cooled to −60 to −70° C., a solution (3.8 mL) of 3 M ethylmagnesium bromide in diethyl ether was added dropwise, the mixture was stirred at −75° C. for 70 min and then at room temperature for 1 h, followed by addition of a solution of Pd(PPh3)4 (0.60 g) and (2,6-dichloropyrimidin-4-yl)dimethylamine (2.0 g) in THF (8 mL), and the mixture was heated to reflux for 17 h. The mixture was cooled to room temperature, then the reaction mixture was diluted with chloroform, washed with saturated aqueous ammonium chloride, and then extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, then the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=15:1) to obtain the title compound (0.18 g) and (6-chloro-2-ethylpyrimidin-4-yl)dimethylamine (0.46 g).

Workup

  1. waitat room temperature for 1 h
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 17 h
  4. temperatureThe mixture was cooled to room temperature
  5. washwashed with saturated aqueous ammonium chloride
  6. extractionextracted with chloroform
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. customthe desiccant was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15:1)

Sources & evidence

ORD record
ord-56462ce290b644fa97caef23c4d5b952
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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