Sodium Hydroxide → HCID 178429705, compound

HRID 425243Notes

Reaction equation

HRID 425243 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:20]#[N:21])[N:12]3[C:17](Cl)=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[C:4]([CH3:22])[CH:3]=1.NC(N)=[S:25].[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:20]#[N:21])[N:12]3[C:17]([SH:25])=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[C:4]([CH3:22])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 58298337HCID 58298337, compound

Product 1

HCID 178429705HCID 178429705, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2-methyl-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (7.50 g), thiourea (7.11 g) in ethanol (50 mL) was heated at reflux for 2 h. The reaction mixture was cooled to room temperature, poured into 0.5 M NaOH aqueous solution, stirred for 1 hour 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: chloroform/methanol=10:1) to give 8-(4-bromo-2,6-dimethyl-phenyl)-4-mercapto-2-methyl-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (7.52 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform/methanol=10:1)

Sources & evidence

ORD record
ord-e58de1046a934772872372fd5513c80d
Source dataset
uspto-grants-2012_01
Patent number
US08106194B2

Reaction notes

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