Sodium Carbonate → 5-(6-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

HRID 12714

Reaction equation

HRID 12714 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][N:16]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:14][C:15]1[N:16]=[CH:17][C:18]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 43971762-Chloro-5-iodopyridine

Product 1

HCID 589942255-(6-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Dimethoxy-pyrimidine-5-boronic acid (1.14 g, 6.26 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-chloro-5-iodopyridine (1 g, 4.2 mmol), Na2CO3 (884 mg, 15.8 mmol), PPh3 (109 mg, 0.42 mmol) and Pd(OAc)2 (46 mg) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated to give the title compound that was used in the next step without further purification (quantitative yield).

Workup

  1. temperatureat reflux for 2.5 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-83a8359273f84a0e9c3c5ff492ad4420
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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