Isobutyryl chloride → HCID 178429167, compound

HRID 591232Notes

Reaction equation

HRID 591232 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)[CH:12]([CH3:14])[CH3:13]>O1CCOCC1.CN(C)C=O>[CH3:10][C:4]1[CH:5]=[C:6]([OH:9])[N:7]2[N:8]=[C:11]([CH:12]([CH3:14])[CH3:13])[N:1]=[C:2]2[N:3]=1

Participants

5

Reactant 2

HCID 62325Isobutyryl chlorideHCID 9131753-Amino-2-imino-6-methyl-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 178429167HCID 178429167, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Intermediate 1 (0.35 g, 2.497 mmol) and iso-butyryl chloride (FLUKA, 0.262 mL, 2.497 mmol) in a mixture of 1,4-dioxane (4 mL) and N,N-dimethylformamide (1 mL) was heated under reflux overnight. The reaction was then concentrated under vacuum and the residue was purified by flash chromatography (Si, eluting with DCM:MeOH mixtures, gradient from 100:0% to 90:10%) to yield the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction was then concentrated under vacuum
  4. customthe residue was purified by flash chromatography (Si, eluting with DCM:MeOH mixtures, gradient from 100:0% to 90:10%)

Sources & evidence

ORD record
ord-947b58105c184ffc98d225fe3f7f7908
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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