Hydrochloric Acid → 7-Chloroimidazo[1,2-c]pyrimidin-5-ol

HRID 1852953Notes

Reaction equation

HRID 1852953 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[C:7](SC)[N:6]2[CH:11]=[CH:12][N:13]=[C:5]2[CH:4]=1.[OH-:14].[K+].CS.Cl>CO.O>[Cl:2][C:3]1[NH:8][C:7](=[O:14])[N:6]2[CH:11]=[CH:12][N:13]=[C:5]2[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 878MethanethiolHCID 14797Potassium HydroxideHCID 866852967-Chloro-5-(methylthio)imidazo[1,2-c]pyrimidine hydrochloride

Product 1

HCID 213201027-Chloroimidazo[1,2-c]pyrimidin-5-olYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7-Chloro-5-(methylthio)imidazo[1,2-c]pyrimidine hydrochloride (10.5 g, 44.5 mmol) was partially dissolved in MeOH (40 mL) and then a solution of potassium hydroxide (11.2 g, 200 mmol) in water (100 mL) was slowly added and the reaction was heated to reflux. The reaction generates methane thiol, so caution was taken to contain this noxious gas in the hood. After 2 hours the reaction was cooled and then neutralized with a solution of 1N HCl to reach a pH of between 6 and 7. The reaction was filtered and the solid was washed with MeOH. The solids were dried on the filter cake and then dried on a high vacuum pump to provide 7-chloroimidazo[1,2-c]pyrimidin-5(6H)-one (6.6 g, 87% yield) as a white solid. MS (apci) m/z=170.1 (M+H).

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperatureAfter 2 hours the reaction was cooled
  3. filtrationThe reaction was filtered
  4. washthe solid was washed with MeOH
  5. customThe solids were dried on the filter cake
  6. customdried on a high vacuum pump

Sources & evidence

ORD record
ord-6842477620a14f49a15ce5f184133153
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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