Sodium Carbonate → 2-(Methylthio)-4-(pyridin-3-yl)pyrimidine

HRID 1514436Notes

Reaction equation

HRID 1514436 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12](B(O)O)[CH:11]=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]>[CH3:9][S:8][C:4]1[N:3]=[C:2]([C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][N:5]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 971134-Chloro-2-methylthiopyrimidineHCID 27343783-Pyridinylboronic acid

Product 1

HCID 28242882-(Methylthio)-4-(pyridin-3-yl)pyrimidineYield 93.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-chloro-2-methylsulfanyl-pyrimidine (1.00 g, 6.22 mmol), 3-pyridine-boronic acid (918 mg, 7.47 mmol), Na2CO3 (791 mg, 7.47 mmol), triphenylphosphine (162 mg, 0.62 mmol) in nPrOH (60 ml), Pd(OAc)2 (41 mg, 0.19 mmol) was added and 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 (25-0.1-0.1 to 20-0.2-0.2) to give the title compound (1.18 g, 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 (25-0.1-0.1 to 20-0.2-0.2)

Sources & evidence

ORD record
ord-edb7565e964d499ea2df39a9d6748d55
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

Loading…