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

HRID 591235Notes

Reaction equation

HRID 591235 reaction equation
[CH:1]1([C:4]2[N:14]=[C:7]3[N:8]=[C:9]([CH3:13])[CH:10]=[C:11](O)[N:6]3[N:5]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:17])=O.C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:17][C:11]1[N:6]2[N:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[N:14]=[C:7]2[N:8]=[C:9]([CH3:13])[CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178429156HCID 178429156, compound

Product 1

HCID 533918677-Chloro-2-cyclopropyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of Intermediate 19 (0.15 g, 0.789 mmol) in phosphorous oxychloride (ALDRICH, 1 ml, 10.73 mmol) was heated under reflux for 1 h. The reaction mixture was added dropwise into iced water, neutralized with solid Na2CO3 and product was extracted with DCM. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The crude mixture was purified by flash chromatography (Si, eluting with Hexane:EtOAc mixtures from 100:0 to 40:60%) to yield the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. extractionwas extracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe crude mixture was purified by flash chromatography (Si, eluting with Hexane:EtOAc mixtures from 100:0 to 40:60%)

Sources & evidence

ORD record
ord-938d12da529f46dc835c62c688962d15
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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