Water → HCID 67508203, compound

HRID 2172866Notes

Reaction equation

HRID 2172866 reaction equation
[Cl:1][C:2]1[C:3](I)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[Br-].[CH3:12][C:13]1[C:14]([Zn+])=[N:15][CH:16]=[CH:17][CH:18]=1.CCOC(C)=O.O>C1COCC1.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:1][C:2]1[C:3]([C:14]2[C:13]([CH3:12])=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 13973342HCID 13973342, compoundHCID 178426320HCID 178426320, compound

Product 1

HCID 67508203HCID 67508203, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-chloro-4-iodo-2-(methylthio)pyrimidine (5 g, 17.4 mmol) and Pd(PPh3)4 (1 g, 0.87 mmol) in dry THF (120 mL) was degassed under N2 three times. Then a solution of (3-methylpyridin-2-yl)zinc(II) bromide in THF (0.5 M, 53 mL, 26.3 mmol) was added. The resulting mixture was heated at reflux overnight. The mixture was then cooled to room temperature and was treated with EtOAc (80 mL) and H2O (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine (50 mL), dried over Na2SO4 and filtered. The filtrate was concentrated and filtered. The filtrate was concentrated and the residue was purified via column chromatography (petroleum ether: EtOAc=9:1) to give the title compound (2.8 g, 64%) as a yellow syrup.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (50 mL×3)
  5. washThe combined organic layers were washed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customthe residue was purified via column chromatography (petroleum ether: EtOAc=9:1)

Sources & evidence

ORD record
ord-0dac01a229284fb991865b725d13acdd
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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