Chloroacetic Acid → HCID 178439470, compound

HRID 449886Notes

Reaction equation

HRID 449886 reaction equation
ClCC(O)=[O:4].[CH:6]([C:9]1[N:14]=[C:13](S)[N:12]=[C:11]([OH:16])[CH:10]=1)([CH3:8])[CH3:7].Cl>O>[CH:6]([C:9]1[N:14]=[C:13]([OH:4])[N:12]=[C:11]([OH:16])[CH:10]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 178439475HCID 178439475, compound

Product 1

HCID 178439470HCID 178439470, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloroacetic acid (22 g, 0.23 mol) and 6-isopropyl-2-mercaptopyrimidin-4-ol (10 g, 59 mmol) were suspended in water (150 mL). The reaction mixture was refluxed for 6 hours. Concentrated HCl (0.36 mL) was added carefully, and the reaction was returned to reflux for 12 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure to give 6-isopropylpyrimidine-2,4-diol (9.0 g, yield: 100%), which was used in the next step without further purification. LCMS (ESI) m/z: 155.0 [M+H+].

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. temperatureto reflux for 12 hours
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a03b59734ebe4e1290b974193c22526a
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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