Potassium Phosphate, Tribasic → 2-Chloro-5-cyclopropylpyrimidine

HRID 467465Notes

Reaction equation

HRID 467465 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1.O>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([CH:9]2[CH2:11][CH2:10]2)=[CH:7][N:6]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 6066655-Bromo-2-chloropyrimidineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 468640872-Chloro-5-cyclopropylpyrimidine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

3.60 g (18.6 mmol) 5-bromo-2-chloropyrimidine, 4.80 g (55.8 mmol) cyclopropyl boronic acid, 13.8 g (65.1 mmol) K3PO4, 568 mg (2.03 mmol) tricyclohexylphosphine and 4 mL water are added to 80 mL toluene. The mixture is degassed thoroughly and charged with 627 mg (2.79 mmol) Pd(OAc)2. After degassing again the mixture is stirred at 100° C. over night, filtered and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc 90/10 70/30).

Workup

  1. customThe mixture is degassed thoroughly
  2. customAfter degassing again the mixture
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc 90/10 70/30)

Sources & evidence

ORD record
ord-a6fe83f072f54eba8f28d6855c29e085
Source dataset
uspto-grants-2014_01
Patent number
US08623860B2

Reaction notes

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