Sodium Hydroxide → HCID 58298339, compound

HRID 425245Notes

Reaction equation

HRID 425245 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:21]#[N:22])[N:12]3[C:17]([S:18][CH3:19])=[CH:16][C:15]([CH3:20])=[N:14][C:13]=23)=[C:4]([CH3:23])[CH:3]=1.[OH-:24].[Na+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:21]([NH2:22])=[O:24])[N:12]3[C:17]([S:18][CH3:19])=[CH:16][C:15]([CH3:20])=[N:14][C:13]=23)=[C:4]([CH3:23])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58298344HCID 58298344, compound

Product 1

HCID 58298339HCID 58298339, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-methylsulfanyl-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (5.70 g) was added into conc. H2SO4 (100 mL) and heated for 60° C. for 5 hours. The reaction mixture was cooled to room temperature, poured into ice-water and then 10% aqueous NaOH solution was added to make the aqueous mixture alkaline (pH=8) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: ethyl acetate) to give 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-methylsulfanyl-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid amide (3.12 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: ethyl acetate)

Sources & evidence

ORD record
ord-b1365ab772a24a91b00916895c99f5c8
Source dataset
uspto-grants-2012_01
Patent number
US08106194B2

Reaction notes

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