Cesium carbonate → HCID 67408142, compound

HRID 869286Notes

Reaction equation

HRID 869286 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([O:10][CH3:11])=[CH:4][N:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=1[C:22]([F:25])([F:24])[F:23].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.ClCCl.[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:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[N:7]([CH3:8])[C:6](=[O:9])[C:5]([O:10][CH3:11])=[CH:4][N:3]=2)=[CH:15][C:14]=1[C:22]([F:23])([F:24])[F:25]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27826714-Chloro-3-(trifluoromethyl)benzeneboronic acidHCID 66519725HCID 66519725, compound

Product 1

HCID 67408142HCID 67408142, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 500 mg (2.86 mmol) 2-chloro-5-methoxy-3-methylpyrimidin-4(3H)-one in 10 ml THF was added 233 mg (0.286 mmol) 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct, 0.965 g (4.29 mmol) 4-chloro-3-(trifluoromethyl)benzeneboronic acid, and 1.87 g (5.73 mmol) Cs2CO3. The reaction mixture was heated to 130° C. for 15 min in the microwave, then diluted with 10 ml water, extracted with 30 ml EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography (25 g silica gel, 40-100% hexane/EtOAc) gave 625 mg (68% yield) of 2-[4-chloro-3-(trifluoromethyl)phenyl]-5-methoxy-3-methylpyrimidin-4(3H)-one. LCMS [M+H]+=319.1.

Workup

  1. extractionextracted with 30 ml EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (25 g silica gel, 40-100% hexane/EtOAc)

Sources & evidence

ORD record
ord-fb35d5d8115a45b2a3e86fc6331f3597
Source dataset
uspto-grants-2015_03
Patent number
US08969364B2

Reaction notes

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