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

HRID 591233Notes

Reaction equation

HRID 591233 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](O)[N:5]2[N:9]=[C:10]([CH:12]([CH3:14])[CH3:13])[N:11]=[C:4]2[N:3]=1.P(Cl)(Cl)([Cl:17])=O.C([O-])([O-])=O.[Na+].[Na+]>O>[Cl:17][C:6]1[N:5]2[N:9]=[C:10]([CH:12]([CH3:14])[CH3:13])[N:11]=[C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178429167HCID 178429167, compound

Product 1

HCID 533918637-Chloro-5-methyl-2-(1-methylethyl)[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of Intermediate 17 (0.225 g, 1.171 mmol) in phosphorous oxychloride (ALDRICH, 0.327 ml, 3.51 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. A brown oil was obtained upon solvent removal in vacuo which 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. customA brown oil was obtained upon solvent removal in vacuo which
  7. customwas purified by flash chromatography (Si, eluting with Hexane:EtOAc mixtures from 100:0 to 40:60%)

Sources & evidence

ORD record
ord-36824fea01cc4572a3716e4a9506d30b
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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