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

HRID 12730Notes

Reaction equation

HRID 12730 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]=[C:15]([CH3:22])[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]=[C:15]([CH3:22])[N:14]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2634165-Iodo-2,4-dimethoxypyrimidineHCID 27631272-Chloro-6-methylpyridine-3-boronic acid

Product 1

HCID 589942175-(2-Chloro-6-methyl-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Dimethoxy-5-iodopyrimidine (957 mg, 3.59 mmol) was dissolved in degassed n-PrOH (18 ml) and then 2-chloro-6-methylpyridine-3-boronic acid (923 mg, 5.39 mmol), Na2CO3 (761 mg, 7.2 mmol), PPh3 (94 mg, 0.35 mmol) and Pd(OAc)2 (40 mg) were added. The suspension was stirred at reflux for 3 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 3 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-a4c85c3e9498464ba3062577b6f704f4
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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