Water → HCID 22482764, compound

HRID 2182073Notes

Reaction equation

HRID 2182073 reaction equation
[NH2:1][C:2]1[N:3]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Br:17])=[CH:12][C:11]=2[Br:18])[CH:4]=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:19](OC(=O)C)(=[O:21])[CH3:20].O>C(O)(=O)C>[C:7]([C:6]1[C:5]([CH3:9])=[CH:4][N:3]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Br:17])=[CH:12][C:11]=2[Br:18])[C:2]=1[NH:1][C:19](=[O:21])[CH3:20])#[N:8]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 22482744HCID 22482744, compound

Product 1

HCID 22482764HCID 22482764, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 5 ml of acetic acid, 1.9 g of 2-amino-4-methyl-1-(2,4-dibromo-6-chlorophenyl)pyrrole-3-carbonitrile and 1.48 g of acetic anhydride were dissolved. The reaction mixture was heated under reflux for 30 minutes. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. Subsequently, the extract was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure to yield crude N-[3-cyano-4-methyl-1-(2,4-dibromo-6-chlorophenyl)-1H-pyrrol-2-yl]acetamide. To the obtained crude N-[3-cyano-4-methyl-1-(2,4-dibromo-6-chlorophenyl)-1H-pyrrol-2-yl]acetamide, 8 ml of 85% phosphoric acid were added. The reaction mixture was heated for 0.5 hours at 130° C., and subsequently, water was added thereto. The reaction mixture was extracted with chloroform, and subsequently, the extract was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) and was allowed to stand for crystallization. The precipitated crystals were washed with ethyl acetate to yield 1.1 g of 2,5-dimethyl-7-(2,4-dibromo-6-chlorophenyl)-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialSubsequently, the extract was dried over anhydrous sodium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b24891fc66bb447786f8203474b243c6
Source dataset
uspto-grants-2005_05
Patent number
US06894168B2

Reaction notes

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