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Potassium Phosphate, Tribasic → (E)-4-chloro-6-(4-chlorostyryl)pyrimidine

HRID 2059878
Notes
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Reaction equation

HRID 2059878 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:20]=[CH:19][C:13](/[CH:14]=[CH:15]/B(O)O)=[CH:12][CH:11]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.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:7]=[C:2](/[CH:15]=[CH:14]/[C:13]2[CH:19]=[CH:20][C:10]([Cl:9])=[CH:11][CH:12]=2)[N:3]=[CH:4][N:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 709434,6-DichloropyrimidineHCID 642694trans-2-(4-Chlorophenyl)vinylboronic acid

Product 1

HCID 58579925(E)-4-chloro-6-(4-chlorostyryl)pyrimidineYield 24.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compound
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of commercially available 4,6-dichloropyrimidine (300 mg, 2.01 mmol), (E)-4-chlorostyrylboronic acid (441 mg, 2.41 mmol), potassium phosphate (1282 mg, 6.04 mmol), and PalladiumTetrakis (116 mg, 0.10 mmol) in DMF (1 mL) was stirred under nitrogen at 40° C. for 2 days. The reaction was filtered, diluted with CH2Cl2, washed with water, brine, dried (MgSO4), and concentrated. The crude product was purified using ISCO flash chromatography (silica gel/hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford the desired product (E)-4-chloro-6-(4-chlorostyryl)pyrimidine 20A (120 mg, 0.49 mmol, 23.73% yield) as a light yellow solid. LC/MS 252 (M+H)+, tR 1.07 min (method 5).

Workup

  1. filtrationThe reaction was filtered
  2. additiondiluted with CH2Cl2
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-5c24e7569c4f40c9ba07ab9d1abe1618
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08278316B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes