Water → HCID 17881917, compound

HRID 1821357Notes

Reaction equation

HRID 1821357 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[NH2:10][C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1.O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=C(P(C1C=CC=CC=1)C1C=CC=CC=1)C=2.C(=O)([O-])[O-].[Cs+].[Cs+]>[N:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:11]=1[NH:10][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

8

Reactant 3

HCID 962WaterHCID 79782-AminopyrimidineHCID 811292-Bromobenzaldehyde

Product 1

HCID 17881917HCID 17881917, compoundYield 64%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 12045512HCID 12045512, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-bromobenzaldehyde (0.35 mL, 3.0 mmol), 2-aminopyrimidine (0.34 g, 3.6 mmol), tris(dibenzylideneacetone)dipalladium (28 mg, 0.030 mmol), 9,9-dimethyl-4,6-bis(diphenylphosphino)xanthene (38 mg, 0.066 mmol) and cesium carbonate (28 mg, 0.030 mmol) in 1,4-dioxane (6.0 mL) was stirred at 100° C. for 19 hours under argon atmosphere. After cooling to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane to hexane/ethyl acetate=8/2) to obtain 2-(2-pyrimidylamino)benzaldehyde (0.38 g, 64%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane to hexane/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-3e72590f51ca4d83a003b336d36e97b9
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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