Sodium Carbonate → HCID 59242775, compound

HRID 1514423Notes

Reaction equation

HRID 1514423 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[CH3:10][C:11]1[CH:16]=[C:15](B(O)O)[CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][C:11]1[CH:16]=[C:15]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)[CH:14]=[CH:13][N:12]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 971134-Chloro-2-methylthiopyrimidineHCID 41926642-Methylpyridine-4-boronic acid

Product 1

HCID 59242775HCID 59242775, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-chloro-2-methylsulfanyl-pyrimidine (781 mg, 4.86 mmol) in degassed nPrOH (55 ml), 2-methylpyridine-4-boronic acid (800 mg, 5.84 mmol), Na2CO3 (619 mg, 5.47 mmol), triphenylphosphine (127 mg, 0.486 mmol) and Pd(OAc)2 (32 mg, 0.15 mmol) were added. The mixture was stirred at 100° C. for 1 hour. The solvent was evaporated under vacuum, and the crude was dissolved in DCM and washed with water. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (20-0.1-0.2) to give 990 mg of the title compound (93% yield).

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe crude was dissolved in DCM
  3. washwashed with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (20-0.1-0.2)

Sources & evidence

ORD record
ord-c6550bf1df4a4a43ab340601c1fa409f
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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