Potassium Phosphate, Tribasic → 4-Chloro-6-(4-fluorophenyl)-2-(2-(S)-methylpyrrolidin-1-yl)pyrimidine

HRID 1444145Notes

Reaction equation

HRID 1444145 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[CH3:14])[N:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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:8][C:6]1[CH:7]=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)[N:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[CH3:14])[N:5]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 591682744,6-Dichloro-2-(2-(S)-methylpyrrolidin-1-yl)pyrimidine

Product 1

HCID 591683784-Chloro-6-(4-fluorophenyl)-2-(2-(S)-methylpyrrolidin-1-yl)pyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 4,6-dichloro-2-(2-(S)-methylpyrrolidin-1-yl)pyrimidine (2.25 g, 9.74 mmol), 4-fluorophenylboronic acid (10.23 mmol), Pd(PPh3)4 (562 mg, 0.487 mmol), and a 2M potassium phosphate solution (9.74 mL) in dioxane (35 mL) under nitrogen at 80° C. for 16 h. Evaporate the mixture and add water (50 mL). Extract with EtOAc (3×50 mL), dry (Na2SO4), and evaporate. Purify by SiO2 flash chromatography, eluting with 9:1 hexanes:EtOAc to provide the title compound as an oil.

Workup

  1. temperatureHeat
  2. customEvaporate the mixture
  3. additionadd water (50 mL)
  4. extractionExtract with EtOAc (3×50 mL)
  5. dry with materialdry (Na2SO4)
  6. customevaporate
  7. customPurify by SiO2 flash chromatography
  8. washeluting with 9:1 hexanes

Sources & evidence

ORD record
ord-96c2e41194964e4fbe0dd8a013207b88
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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