Sodium Bicarbonate → HCID 67519692, compound

HRID 1925034Notes

Reaction equation

HRID 1925034 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:8])[S:5][C:6]=1[CH3:7].[CH3:9][O:10][C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14](B(O)O)=[CH:13][N:12]=1.C(=O)(O)[O-].[Na+]>COCCOC.C(Cl)Cl.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>[CH3:8][C:4]1[S:5][C:6]([CH3:7])=[C:2]([C:14]2[C:15]([O:17][CH3:18])=[N:16][C:11]([O:10][CH3:9])=[N:12][CH:13]=2)[N:3]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 567767374-Bromo-2,5-dimethyl-1,3-thiazole

Product 1

HCID 67519692HCID 67519692, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-bromo-2,5-dimethyl-1,3-thiazole (commercially available from Apollo Scientific Ltd, 410 mg, 2.135 mmol) in 1,2-Dimethoxyethane (DME) (6.5 mL), Tetrakis(triphenylphosphine)palladium (123 mg, 0.107 mmol) was added and the mixture was stirred at rt for 30 minutes. Then [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich, 916 mg, 4.48 mmol) and 1M Sodium bicarbonate aqueous solution (5.83 mL, 5.83 mmol) were added. The reaction mixture was then stirred at 90° C. for 2.5 h and left stirring at rt overnight. The day after the mixture was diluted with DCM and washed with water. Organic layer was dried and concentrated under vacuum. Crude product was first purified by flash chromatography (eluent: Cy/AcOEt 65:35) and further purified by SCX cartridge affording 5-(2,5-dimethyl-1,3-thiazol-4-yl)-2,4-bis(methyloxy)pyrimidine with minor unknown impurities that was used in the next step without further purification.

Workup

  1. stirringThe reaction mixture was then stirred at 90° C. for 2.5 h
  2. waitleft
  3. stirringstirring at rt overnight
  4. washwashed with water
  5. customOrganic layer was dried
  6. concentrationconcentrated under vacuum
  7. customCrude product was first purified by flash chromatography (eluent: Cy/AcOEt 65:35)
  8. customfurther purified by SCX cartridge

Sources & evidence

ORD record
ord-85610dc19fa343e6952e1646ef2367d0
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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