4,4-Dimethyl-2-pentanone → 4-Neopentylpyrimidine

HRID 1042404Notes

Reaction equation

HRID 1042404 reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4](=O)[CH3:5].[C:9](O)(=O)C.[CH:13]([NH2:15])=[NH:14]>C(O)CCC>[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]1[CH:5]=[CH:9][N:15]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 115464,4-Dimethyl-2-pentanoneHCID 160693Formamidine acetate

Product 1

HCID 450803944-NeopentylpyrimidineYield 33.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 4,4-dimethyl-pentan-2-one (10 g, 0.1 mol), formamidine acetate (57 g, 0.5 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-(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-99991a9426a44b029d762a7b8b044f82
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

Loading…