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

HRID 12718Notes

Reaction equation

HRID 12718 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](I)=[CH:5][N:4]=1.[Cl:12][C:13]1[C:18](B(O)O)=[CH:17][CH:16]=[CH:15][N:14]=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:12][C:13]1[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:17][CH:16]=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2634165-Iodo-2,4-dimethoxypyrimidineHCID 2762704(2-Chloropyridin-3-yl)boronic acid

Product 1

HCID 589942445-(2-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Dimethoxy-5-iodo-pyrimidine (1 g, 3.76 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-chloropyridine-3-boronic acid (882 mg, 5.61 mmol), Na2CO3 (800 mg, 7.6 mmol), PPh3 (98 mg, 0.37 mmol) and Pd(OAc)2 (40 mg, 0.19 mmol) were added. The suspension was stirred at reflux for 4 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 without further purification in the next step (quantitative yield).

Workup

  1. temperatureat reflux for 4 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-39e094d93f7f4d7f97b94ae4898ea550
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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