Pyridine → HCID 10012287, compound

HRID 1809186Notes

Reaction equation

HRID 1809186 reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5](O)=[N:4][CH:3]=1.N1C=CC=CC=1.[OH-].[Na+].O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:5]1[C:6]2[N:7]([CH:8]=[CH:9][N:10]=2)[C:2]([CH3:1])=[CH:3][N:4]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178430682HCID 178430682, compound

Product 1

HCID 10012287HCID 10012287, compoundYield 26%

Conditions

Temperature
120 °C

Procedure

To a solution of 5-Methyl-imidazo[1,2-a]pyrazin-8-ol (1.32 g, 8.86 mmol) in POCl3 (25 mL) is added pyridine (0.53 mL, 6.6 mmol) and the reaction stirred at 120° C. under N2 atmosphere for 4 h 30 min. The reaction is cooled to 60° C. and poured into 80 g of ice and stirred for 1 h. The mixture is neutralized with NaOH (20%), extracted with CHCl3/IPA 9/1, dried with MgSO4 anh., filtered and concentrated to get a crude that is purified by column chromatography using a gradient of (DCM/MeOH:98/2 to 95/5) to give 8-Chloro-5-methyl-imidazo[1,2-a]pyrazine as a pale yellow solid (0.39 g, 26%).

Workup

  1. temperatureThe reaction is cooled to 60° C.
  2. stirringstirred for 1 h
  3. extractionextracted with CHCl3/IPA 9/1
  4. dry with materialdried with MgSO4 anh.
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto get a crude that
  8. customis purified by column chromatography

Sources & evidence

ORD record
ord-e553e2cddece417b8e7ad2c401092189
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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