Potassium Phosphate, Tribasic → HCID 57990358, compound

HRID 2381772Notes

Reaction equation

HRID 2381772 reaction equation
Br[C:2]1[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11][CH2:10]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:24]1(B(O)O)[CH2:26][CH2:25]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[Cl:8][C:5]1[N:4]=[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11][CH2:10]2)[C:2]([CH:24]2[CH2:26][CH2:25]2)=[CH:7][N:6]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 57990385HCID 57990385, compound

Product 1

HCID 57990358HCID 57990358, compoundYield 128.4%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl (1-(5-bromo-2-chloropyrimidin-4-yl)piperidin-4-yl)methylcarbamate (112 mg, 0.276 mmol), cyclopropylboronic acid (40 mg, 0.465 mmol), K3PO4 (200 mg, 0.943 mmol) and tricyclohexyl phosphine (20 mg, 0.071 mmol) in toluene (3 mL) and H2O (0.2 mL) was degassed with argon, then Pd(OAc)2 (10 mg, 0.044 mmol) was added. The mixture was stirred at 100° C. for 20 h. Water and EtOAc were added. The organic phase was separated, washed with brine, dried over Na2SO4, concentrated in vacuo to give tert-butyl (1-(2-chloro-5-cyclopropylpyrimidin-4-yl)piperidin-4-yl)methycarbamate (130 mg).

Workup

  1. customwas degassed with argon
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7317a8d9b2a4af0bc23e81a1abc54a8
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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