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

HRID 241344
Notes
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Reaction equation

HRID 241344 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 178418397
HCID 178418397, compound
Catalyst
HCID 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-5c6d9517c3994f43a4f9fd7b6adb900d
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08648197B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes