Sodium Carbonate → 2-Chloro-4-(2-methyl-3-furanyl)pyrimidine

HRID 2278435Notes

Reaction equation

HRID 2278435 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:21]=[CH:20][O:19][C:18]=2[CH3:22])O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:17]2[CH:21]=[CH:20][O:19][C:18]=2[CH3:22])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 242295474,4,5,5-Tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolane

Product 1

HCID 867024262-Chloro-4-(2-methyl-3-furanyl)pyrimidineYield 52.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2,4-Dichloropyrimidine (1.0 g, 6.71 mmol), 4,4,5,5-tetramethyl-2-(2-methyl-3-furanyl)-1,3,2-dioxaborolane (1.397 g, 6.71 mmol), sodium carbonate (1.067 g, 10.07 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.388 g, 0.336 mmol) were added together in 1,4-dioxane (42 mL) and water (7.00 mL) and the resulting mixture was heated at 85° C. under argon for 4 hours. The reaction mixture was allowed to cool to room temperature, diluted with water and extracted with ethyl acetate (×3). The ethyl acetate layers were combined, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by Biotage SP4 column chromatography eluting with a gradient of 0-30% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound (686 mg, 3.52 mmol, 52.5 yield) as a white solid. LC/MS [M+H]+=195/197.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by Biotage SP4 column chromatography
  5. washeluting with a gradient of 0-30% ethyl acetate and iso-hexane
  6. additionProduct containing fractions
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0b5ba0727c84491393215d2bff27ea55
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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