Cesium carbonate → HCID 117677654, compound

HRID 1507496Notes

Reaction equation

HRID 1507496 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([S:9][CH3:10])[N:6]=[C:5]([NH:11][CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)[C:4]=1B1OC(C)(C)C(C)(C)O1.Br[C:35]1[N:40]=[CH:39][C:38]([F:41])=[CH:37][N:36]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(OCC)(=O)C.[Pd+2].Cl[Cu]>[F:41][C:38]1[CH:37]=[N:36][C:35]([C:4]2[C:5]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:13]3)=[N:6][C:7]([S:9][CH3:10])=[N:8][C:3]=2[O:2][CH3:1])=[N:40][CH:39]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 263440482-Bromo-5-fluoropyrimidineHCID 131734377HCID 131734377, compound

Product 1

HCID 117677654HCID 117677654, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In a 40 mL vial, chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl)]palladium(II) (0.025 g, 0.031 mmol), tert-butyl 3-((6-methoxy-2-(methylthio)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-4-yl)amino)piperidine-1-carboxylate (0.15 g, 0.312 mmol), 2-bromo-5-fluoropyrimidine (0.083 g, 0.468 mmol) and CuCl (0.031 g, 0.312 mmol) were combined, then purged with argon. Then degassed DMF (3 mL) followed by Cs2CO3 (0.407 g, 1.249 mmol) were added to the vial. The reaction was then heated at 100° C. for 18 h. The mixture was cooled, diluted with ethyl acetate, washed with water, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The material was purified by column chromatography on silica gel (0-100% EtOAc in hexanes) to afford the desired product. MS (m/z)=451 (M+H).

Workup

  1. custompurged with argon
  2. additionwere added to the vial
  3. temperatureThe mixture was cooled
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe material was purified by column chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b7237195e22249d1a1daa1156941e145
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

Loading…