2,2,5,5-Tetramethyl-3-hexanone → HCID 21135795, compound

HRID 1042406Notes

Reaction equation

HRID 1042406 reaction equation
[CH3:1][C:2]([CH3:11])([C:4](=O)[CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:3].[C:12](O)(=O)C.[CH:16]([NH2:18])=[NH:17]>C(O)CCC>[C:2]([C:4]1[C:5]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:12][N:18]=[CH:16][N:17]=1)([CH3:11])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 1366702,2,5,5-Tetramethyl-3-hexanoneHCID 160693Formamidine acetate

Product 1

HCID 21135795HCID 21135795, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 2,2,5,5-tetramethyl-hexan-3-one (10 g, 0.06 mol), formamidine acetate (33 g, 0.3 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-di-tert-butyl-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-d998b382f77b4e5fb204f88317e49027
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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