Sodium Carbonate → HCID 24901862, compound

HRID 1927824Notes

Reaction equation

HRID 1927824 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[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+]>C(COC)OC.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:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

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

Product 1

HCID 24901862HCID 24901862, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2,4-dichloropyrimidine (3.1 g, 20 mmol), 4-chlorophenylboronic acid (3.0 g, 20 mmol), and tetrakis(triphenylphosphine)palladium (0.69 g, 0.6 mmol) in dimethoxyethane (200 mL)/sat. Na2CO3 solution (34 mL) was heated to 80° C. for 20 h. The cooled mixture was poured into ice-water and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried and evaporated. The crude product was purified by chromatography on silica gel using ethyl acetate/cyclohexane (1:2, v/v) as eluent to give the title compound (1.82 g, 40%) as white solid. NMR (DMSO-d6) δ 7.67 (d, 2 H, J, J=7 Hz), 8.19 (d, 2 H, J=5 Hz), 8.23 (d, 2 H, J=7 Hz), 8.86 (d, 2 H, J=5 Hz) ppm; mp 290-292° C.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2502ecd9b017494eb7329e8f38b0f5eb
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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