Sodium Carbonate → HCID 79079991, compound

HRID 707258Notes

Reaction equation

HRID 707258 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:23][C:24]1[N:29]=[C:28](Cl)[CH:27]=[CH:26][N:25]=1>O1CCOCC1.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:23][C:24]1[N:29]=[C:28]([C:5]2[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:27]=[CH:26][N:25]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 164142722-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 79079991HCID 79079991, compoundYield 47.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.65 g, 2.89 mmol), sodium carbonate (0.610 g, 5.80 mmol), 2,4-dichloropyrimidine (0.430 g, 2.89 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(ii) dichloride (0.100 g, 0.15 mmol) in a mixture of dioxane (20 mL) and water (4 mL) was stirred and heated at 40° C. for 10 hours. The mixture was filtered through CELITE™ and washed with dichloromethane. The filtrate was evaporated in vacuo and the residue was purified by column chromatography on silica gel (10% to 30% ethyl acetate in petroleum ether) to give 2-chloro-4-(6-methylpyridin-3-yl)pyrimidine (280 mg, 1.36 mmol, 47% yield).

Workup

  1. filtrationThe mixture was filtered through CELITE™
  2. washwashed with dichloromethane
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel (10% to 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-0cbec38ed2724af3923626ce29f3a24c
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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