Ethyl Acetate → 4-Chloro-6-(4-chlorophenyl)pyrimidine

HRID 1920109Notes

Reaction equation

HRID 1920109 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>C1COCC1.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:8][C:6]1[CH:5]=[C:4]([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[N:3]=[CH:2][N:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 775312,4-Dichloropyrimidine

Product 1

HCID 249020894-Chloro-6-(4-chlorophenyl)pyrimidineYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 2,4-dichloro-pyrimidine (1 eq) in THF/H2O (4:3) solution, was added 4-chloro phenyl boronic acid (1 eq), Pd(PPh3)4 (0.01 eq) and Na2CO3 (2 eq) under Ar. The reaction mixture was stirred at reflex for overnight. EtOAc (10 mL) was added. The organic phase was separated, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (Ethyl acetate:Hexane: 1:3) to give the desired product as a white powder (71% yield. MS: (ESI), M/Z, 225 (M+1). Retention time: 1.07 min (FA-non polar).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (Ethyl acetate:Hexane: 1:3)

Sources & evidence

ORD record
ord-c51b376c6c26478081a6611a727ec6b6
Source dataset
uspto-grants-2012_05
Patent number
US08168788B2

Reaction notes

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