2,2,6,6-Tetramethyl-4-heptanone → HCID 70926412, compound

HRID 1042407Notes

Reaction equation

HRID 1042407 reaction equation
[CH3:1][C:2]([CH3:12])([CH2:4][C:5](=O)[CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH3:3].[C:13](O)(=O)C.[CH:17]([NH2:19])=[NH:18]>C(O)CCC>[C:2]([C:4]1[C:5]([CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[N:18][CH:17]=[N:19][CH:13]=1)([CH3:12])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 1382442,2,6,6-Tetramethyl-4-heptanoneHCID 160693Formamidine acetate

Product 1

HCID 70926412HCID 70926412, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 2,2,6,6-tetramethyl-heptan-4-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 5-tert-butyl-4-(2,2-dimethyl-propyl)-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-48e5dd3520264ca19aab8354cc5d0cb1
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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