4,6-Dichloropyrimidine → HCID 21949160, compound

HRID 2376893Notes

Reaction equation

HRID 2376893 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[CH:13][NH:14]3)[CH:7]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 5834314-Aminoindole

Product 1

HCID 21949160HCID 21949160, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4,6-Dichloropyrimidine (1.01 g, 6.6 mmol), 4-aminoindole (900 mg, 6.6 mmol) and N,N-diisopropylethylamine (3.14 ml, 18 mmol) were dissolved in N,N-dimethylformamide (20 ml), and the reaction mixture was stirred at 80° C. for 6 hours. The reaction mixture was partitioned between ethyl acetate and water; the aqueous layer was subjected to re-extraction with ethyl acetate, and the combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure; and a small amount of methanol was added to the residue to crystallize; and the crystals were filtered off, washed with methanol and ethyl acetate, and dried under aeration to yield the title compound (599 mg, 2.5 mmol, 37%) as pale brown crystals.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous layer was subjected to re-extraction with ethyl acetate
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. additionand a small amount of methanol was added to the residue
  7. customto crystallize
  8. filtrationand the crystals were filtered off
  9. washwashed with methanol and ethyl acetate
  10. customdried under aeration

Sources & evidence

ORD record
ord-4d9b53f6efde41b6ac48f003aba8eac3
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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