Pinacolone → 4-(1,1-Dimethylethyl)pyrimidine

HRID 1042403Notes

Reaction equation

HRID 1042403 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](=O)[CH3:4].[C:8](O)(=O)C.[CH:12]([NH2:14])=[NH:13]>C(O)CCC>[C:2]([C:3]1[CH:4]=[CH:8][N:14]=[CH:12][N:13]=1)([CH3:7])([CH3:6])[CH3:1]

Participants

4

Reactant 2

HCID 6416PinacoloneHCID 160693Formamidine acetate

Product 1

HCID 114804734-(1,1-Dimethylethyl)pyrimidineYield 36.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 3,3-dimethyl-butan-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-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-16bc6374884341c8877d8989e475a5d7
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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