Propionyl chloride → HCID 178437547, compound

HRID 591224Notes

Reaction equation

HRID 591224 reaction equation
[NH2:1][C:2]1[N:7]([NH2:8])[C:6](=[O:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[C:11](Cl)(=O)[CH2:12][CH3:13]>O1CCOCC1.CN(C)C=O>[OH:9][C:6]1[N:7]2[N:8]=[C:11]([CH2:12][CH3:13])[N:1]=[C:2]2[N:3]=[C:4]([CH3:10])[CH:5]=1

Participants

5

Reactant 2

HCID 62324Propionyl chlorideHCID 9131753-Amino-2-imino-6-methyl-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 178437547HCID 178437547, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

Intermediate 1 (0.4 g, 2.85 mmol) was allowed to react with propionyl chloride (ALDRICH, 0.372 mL, 4.28 mmol) in a mixture of 1,4-dioxane (8 mL) and N,N-dimethylformamide (2 mL) overnight under refluxing conditions. The reaction was concentrated under vacuum and the residue was purified (silica gel column, eluting with DCM:MeOH mixtures from 100:0 to 90:10%) to obtain 7-hydroxy-2-ethyl-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine (Intermediate 4) as a white solid.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue was purified
  3. wash(silica gel column, eluting with DCM:MeOH mixtures from 100:0 to 90:10%)

Sources & evidence

ORD record
ord-dc33616e69b04e06b8fee7e2166562e6
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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