Triphenylphosphine → HCID 66589954, compound

HRID 1911453Notes

Reaction equation

HRID 1911453 reaction equation
C(=O)([O-])O.[Na+].Cl[C:7]1[N:12]=[CH:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9][N:8]=1.CC1(C)C(C)(C)OB([C:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH:26]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:34]([O:33][C:31]([N:28]1[CH2:27][CH:26]=[C:25]([C:7]2[N:8]=[CH:9][C:10]([C:13]([OH:15])=[O:14])=[CH:11][N:12]=2)[CH2:30][CH2:29]1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Product 1

HCID 66589954HCID 66589954, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Saturated aqueous sodium hydrogen carbonate solution (25.00 ml) was added to methyl 2-chloropyrimidine-5-carboxylate (0.863 g, 5 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.855 g, 6.00 mmol), palladium(II) acetate (0.056 g, 0.25 mmol) and triphenylphosphine (0.262 g, 1.00 mmol) in 1,2-dimethoxyethane (25.00 ml) at 25° C. under nitrogen. The resulting mixture was stirred at 80° C. for 4 h. The cooled reaction mixture was taken up in water (50 mL), washed with EtOAc (50 mL) and then the aqueous layer was acidified to pH1 with 2N HCl. The aqueous layer was extracted with EtOAc (3×25 mL) and the combined organics washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford 2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylic acid (1.280 g, 84%) as a yellow solid. This was used directly with no further purification.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with EtOAc (50 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
  4. washthe combined organics washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6abe3eb7ef34d9ea326e527a7f1ccfd
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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