Sodium Bicarbonate → HCID 59448381, compound

HRID 1925025Notes

Reaction equation

HRID 1925025 reaction equation
Br[C:2]1[CH:3]=[N:4][S:5][CH:6]=1.[CH3:7][O:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12](B(O)O)=[CH:11][N:10]=1.C([O-])(O)=O.[Na+]>COCCOC.O>[S:5]1[CH:6]=[C:2]([C:12]2[C:13]([O:15][CH3:16])=[N:14][C:9]([O:8][CH3:7])=[N:10][CH:11]=2)[CH:3]=[N:4]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 52003584-Bromo-isothiazole

Product 1

HCID 59448381HCID 59448381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

4-bromoisothiazole (commercially available from Aurora, 500 mg, 3.05 mmol) was dissolved in degassed 1,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (176 mg, 0.152 mmol) was added thereto. The reaction mixture was stirred at room temperature for 15 min. [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich, 1178 mg, 6.40 mmol) and 5 mL of degassed 1M/H2O solution of NaHCO3 were added to the reaction mixture under N2 atm. After 2 h 30 min stirring at 90° C. the mixture was diluted with water and extracted with DCM. The collected organic phases were evaporated. The residue was purified by flash chromatography eluting with cyclohexane/EtOAc 5:1. 686 mg of the title compound were isolated as a yellow solid.

Workup

  1. additionwere added to the reaction mixture under N2 atm
  2. extractionextracted with DCM
  3. customThe collected organic phases were evaporated
  4. customThe residue was purified by flash chromatography
  5. washeluting with cyclohexane/EtOAc 5:1

Sources & evidence

ORD record
ord-be916498b32240a1a31a23e5717724ef
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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