2,4-Dichloropyrimidine → HCID 86646783, compound

HRID 913301Notes

Reaction equation

HRID 913301 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]1[CH:12]=[C:11]([Sn](C)(C)C)[N:10]=[CH:9][N:8]=1)[CH3:5].[Cl:17][C:18]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][N:19]=1>CN1CCCC1=O.O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:17][C:18]1[N:23]=[C:22]([C:11]2[CH:12]=[C:7]([NH:6][CH:4]([CH3:5])[CH2:3][O:2][CH3:1])[N:8]=[CH:9][N:10]=2)[CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 67389293HCID 67389293, compound2×

Product 1

HCID 86646783HCID 86646783, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of N-(2-methoxy-1-methylethyl)-6-(trimethylstannyl)-4-pyrimidinamine (i.e., the product of Step B) (0.5 g, 1.51 mmol), 2,4-dichloropyrimidine (0.22 g, 1.51 mmol) and copper iodide (12 mg, 0.061 mmol) in N-methylpyrrolidinone (12 mL) under a nitrogen atmosphere was added bis(triphenylphosphine)palladium(II) dichloride (53 mg, 0.076 mmol). The resulting mixture was stirred at reflux for 2 h. After cooling to room temperature, the solution was diluted with water and extracted with diethyl ether 3 times. The organic layers were combined and washed three times with water, then dried and concentrated. The residue was purified on silica gel using a gradient of 100% hexanes to 40% ethyl acetate in hexanes to afford 270 mg of title compound as a solid.

Workup

  1. temperatureat reflux for 2 h
  2. extractionextracted with diethyl ether 3 times
  3. washwashed three times with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel using a gradient of 100% hexanes to 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b4039a985164457aad341493856fc09b
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

Loading…