Potassium Carbonate → HCID 63318778, compound

HRID 1505670Notes

Reaction equation

HRID 1505670 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[NH2:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>O.O1CCOCC1.CCOC(C)=O.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:1][C:2]1[CH:3]=[N:4][C:5]([C:14]2[CH:15]=[C:10]([CH:11]=[CH:12][CH:13]=2)[NH2:9])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 70066515-Bromo-2-iodopyrimidine

Product 1

HCID 63318778HCID 63318778, compoundYield 96.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-Bromo-2-iodo-pyrimidine (9.0 g; 31.6 mmol; 1.0 eq.), 3-aminophenyl boronic acid (4.3 g; 31.6 mmol; 1.0 eq.), K2CO3 (17.5 g; 126.4 mmol; 4.0 eq.) and Pd(PPh3)4 (1.83 g; 1.58 mmol; 0.05 eq.) in water/dioxane (67:135 mL) was heated overnight at 100° C. The reaction mixture was then diluted with EtOAc and organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated to give the title compound as a beige solid (7.6 g; 96%). HPLC (Condition A): Rt 1.90 min (purity 78.0%). MS (ESI+): 250.1.

Workup

  1. washwas washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7208204183d48f295fd2a9346bac5ea
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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