Sodium Bicarbonate → HCID 11271378, compound

HRID 425241Notes

Reaction equation

HRID 425241 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:27]#[N:28])[N:12]3[C:17]([NH:18][CH:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])=[CH:16][C:15]([CH3:26])=[N:14][C:13]=23)=[C:4]([CH3:29])[CH:3]=1.C(=O)([O-])[OH:31].[Na+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:29])[C:5]([C:9]2[CH:10]=[C:11]([C:27]([NH2:28])=[O:31])[N:12]3[C:17]([NH:18][CH:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])=[CH:16][C:15]([CH3:26])=[N:14][C:13]=23)=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58298342HCID 58298342, compound

Product 1

HCID 11271378HCID 11271378, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
55 °C

Procedure

8-(4-Bromo-2,6-dimethyl-phenyl)-2-methyl-4-(1-propyl-butylamino)-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (10.0 g) was added into conc. H2SO4 (50 mL) and heated for 55° C. for 5 hours. The reaction mixture was cooled to room temperature, poured into ice-water and then a saturated aqueous sodium hydrogencarbonate 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: hexane/ethyl acetate/chloroform=10:3:1) to give a solid. The solid was recrystallized from ethyl acetate to provide 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-(1-propyl-butylamino)-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid amide (5.8 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: hexane/ethyl acetate/chloroform=10:3:1)
  8. customto give a solid
  9. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b07006d8cbf6442ebaf6256f6ab47a10
Source dataset
uspto-grants-2012_01
Patent number
US08106194B2

Reaction notes

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