Water → 5-(4-Bromo-3-fluorophenyl)pyrimidin-2-amine

HRID 1257856Notes

Reaction equation

HRID 1257856 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][C:11]=1[F:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>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>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:12][C:11]=1[F:19]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 2313102-Amino-5-bromopyrimidineHCID 27733354-Bromo-3-fluorobenzeneboronic acid

Product 1

HCID 672238475-(4-Bromo-3-fluorophenyl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-bromopyrimidin-2-amine (2.1 g, 0.012 mol) in 1,4-dioxane (30 mL) was added (4-bromo-3-fluorophenyl)boronic acid (2.0 g, 0.0091 mol), potassium phosphate (6.4 g, 0.030 mol) and tetrakis(triphenylphosphine)palladium (700 mg, 0.6 mmol), water (5 mL). The solution was degassed with N2, and heated at 120° C. for 4 h. The mixture was cooled to RT, poured into water, and extracted with EtOAc. The combined organic layers were washed with brine, dried with MgSO4, filtered, and concentrated. The residue was purified by chromatography on silica gel with EtOAc in CH2Cl2 (0-30%) to afford the desired compound. LCMS: (M+H)=267.9.

Workup

  1. customThe solution was degassed with N2
  2. temperatureThe mixture was cooled to RT
  3. additionpoured into water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel with EtOAc in CH2Cl2 (0-30%)

Sources & evidence

ORD record
ord-263af539a5264077aa1c19607593efa7
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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