3-Hexanone, 2,5-dimethyl- (8CI)(9CI) → HCID 22956096, compound

HRID 1042405Notes

Reaction equation

HRID 1042405 reaction equation
[CH3:1][CH:2]([C:4](=O)[CH2:5][CH:6]([CH3:8])[CH3:7])[CH3:3].[C:10](O)(=O)C.[CH:14]([NH2:16])=[NH:15]>C(O)CCC>[CH:2]([C:4]1[C:5]([CH:6]([CH3:8])[CH3:7])=[CH:10][N:16]=[CH:14][N:15]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 159013-Hexanone, 2,5-dimethyl- (8CI)(9CI)HCID 160693Formamidine acetate

Product 1

HCID 22956096HCID 22956096, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 2,5-dimethyl-hexan-3-one (10 g, 0.08 mol), formamidine acetate (40 g, 0.4 mol), and butanol (50 mL). The reaction mixture is heated to 130° C. and stirred for 24 hours. The crude mass is washed once with aqueous sulfuric acid (10%, 100 mL) followed by twice with brine (30 mL). Butanol is recovered by roto-evaporation. The crude product is further purified with liquid chromatography (Biotage® system) and then crystallized. Product 4,5-diisopropyl-pyrimidine (˜5 g) is obtained.

Workup

  1. customA 100 mL reaction flask
  2. washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
  3. customButanol is recovered by roto-evaporation
  4. customThe crude product is further purified with liquid chromatography (Biotage® system)
  5. customcrystallized

Sources & evidence

ORD record
ord-4549f547729b4506b330b46577f30bed
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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