Sodium Carbonate → 4-(2-Aminopyrimidin-5-yl)-2-fluorophenol

HRID 1257810Notes

Reaction equation

HRID 1257810 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[F:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][C:15]=1[OH:16].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.C1(C)C=CC=CC=1.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>[NH2:8][C:5]1[N:4]=[CH:3][C:2]([C:12]2[CH:13]=[CH:14][C:15]([OH:16])=[C:10]([F:9])[CH:11]=2)=[CH:7][N:6]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 23005361(3-Fluoro-4-hydroxyphenyl)boronic acid

Product 1

HCID 672239574-(2-Aminopyrimidin-5-yl)-2-fluorophenol

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromopyrimidin-2-amine (3.3 g, 19 mmol), (3-fluoro-4-hydroxyphenyl)boronic acid (2.7 g, 17 mmol), tetrakis(triphenylphosphine)palladium (0.6 g, 0.5 mmol), sodium carbonate (18.3 g, 172 mmol) in ethanol (15 mL), water (5 mL) and toluene (15 mL) was heated at 120° C. for 3 h. The volatiles were removed under reduced pressure. The residue was diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered, and concentrated to obtain the desired product which was directly used in the next step.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fdd6c879db604c68aab19409f2cb95be
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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