Sodium Carbonate → 7-Chloro-2-ethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 591225Notes

Reaction equation

HRID 591225 reaction equation
O[C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH3:12])[N:10]=[C:6]2[N:5]=[C:4]([CH3:13])[CH:3]=1.P(Cl)(Cl)([Cl:16])=O.C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:16][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH3:12])[N:10]=[C:6]2[N:5]=[C:4]([CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178437547HCID 178437547, compound

Product 1

HCID 300334477-Chloro-2-ethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The titled compound (Intermediate 5), was obtained by refluxing a suspension of Intermediate 4 (0.3 g, 1.684 mmol) in phosphorus oxychloride (ALDRICH, 1.88 mL, 20.2 mmol) for 2 h and then, adding the reaction mixture slowly to a mixture of water and ice. The solution was neutralized with solid Na2CO3 and extracted with DCM (25 mL). The aqueous layer was further extracted with DCM (2×5 mL) and the combined organic layers were washed with water (20 mL), then with brine (20 mL), and then dried over MgSO4. Solvent was removed under reduced pressure and the crude product was purified (silica gel column, eluting with Hexane/EtOAc mixtures from 100:0 to 40:60%) to obtain Intermediate 5 as a white solid.

Workup

  1. temperatureby refluxing
  2. additionadding the reaction mixture
  3. extractionextracted with DCM (25 mL)
  4. extractionThe aqueous layer was further extracted with DCM (2×5 mL)
  5. washthe combined organic layers were washed with water (20 mL)
  6. dry with materialwith brine (20 mL), and then dried over MgSO4
  7. customSolvent was removed under reduced pressure
  8. customthe crude product was purified
  9. wash(silica gel column, eluting with Hexane/EtOAc mixtures from 100:0 to 40:60%)

Sources & evidence

ORD record
ord-54f0bad1160b4e9bb7b77cecf36fd855
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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