Sulfuric Acid → HCID 22327975, compound

HRID 495668Notes

Reaction equation

HRID 495668 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].OS(O)(=O)=O>C(COC)OC.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.CCCCCC>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[F:9])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 22327975HCID 22327975, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2-amino-5-bromo-pyrimidine 9 (49.40 g, 284 mmol) in dimethoxyethane (500 mL) were added 2-fluorophenylboronic acid 10 (43.66 g, 312 mmol), 2.0 M aqueous sodium carbonate solution (285 mL, 570 mmol) and tetrakis(triphenylphosphine)palladium (0) (3.28 g, 2.84 mmol). The mixture was stirred at reflux for 2 hr. The reaction mixture was cooled to ambient temperature and slowly poured into 10% H2SO4 (600 mL), which was added with hexane (300 mL). The acidic aqueous layer was separated, and the insoluble material and the organic layer was extracted with 10% H2SO4 (200 mL×2). The combined acidic aqueous layers were washed with EtOAc (200 mL), neutralized with K2CO3 to give a precipitate of the title compound and an inorganic salt, which were washed with water (3000 mL) to afford the title compound 11 as a white solid. The white solid was dissolved in hot THF (500 mL). The insoluble material was filtered off and concentrated in vacuo. The residual solid was washed with IPE to afford the title compound 11 as crystals.

Workup

  1. temperatureat reflux for 2 hr
  2. customThe acidic aqueous layer was separated
  3. extractionthe insoluble material and the organic layer was extracted with 10% H2SO4 (200 mL×2)
  4. washThe combined acidic aqueous layers were washed with EtOAc (200 mL)

Sources & evidence

ORD record
ord-019c6ff289584c8f91e6bd396ce4ece5
Source dataset
uspto-grants-2005_09
Patent number
US06939966B2

Reaction notes

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