4,6-Dichloropyrimidine → HCID 21949278, compound

HRID 2376889Notes

Reaction equation

HRID 2376889 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:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2.C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)[CH:7]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 788675-AminoindoleHCID 81531Diisopropylethylamine

Product 1

HCID 21949278HCID 21949278, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

4,6-Dichloropyrimidine (5.89 g, 40 mmol), 5-aminoindole (6.27 g, 47 mmol) and N,N-diisopropylethylamine (20.6 ml, 0.12 mol) were dissolved in N-methylpyrrolidone (80 ml), and the reaction mixture was stirred at 50° C. for 2.5 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; a small amount of ethyl acetate was added to the residue to crystallize; and the crystals were filtered off, washed with diethyl ether, and dried under aeration to yield the title compound (3.70 g, 15 mmol, 38%) as white 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. washand the 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. additiona small amount of ethyl acetate was added to the residue
  7. customto crystallize
  8. filtrationand the crystals were filtered off
  9. washwashed with diethyl ether
  10. customdried under aeration

Sources & evidence

ORD record
ord-e17b41c7db9b4757a2b7bdd91013db1b
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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