Formamidine acetate → HCID 70926291, compound

HRID 1042411Notes

Reaction equation

HRID 1042411 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([CH3:8])[C:4]([CH3:10])([CH3:9])[C:3]=1[CH2:11][CH2:12][C:13](=O)[CH3:14].[C:16](O)(=O)C.[CH:20]([NH2:22])=[NH:21]>C(O)CCC>[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([CH3:8])[C:4]([CH3:10])([CH3:9])[C:3]=1[CH2:11][CH2:12][C:13]1[CH:14]=[CH:16][N:22]=[CH:20][N:21]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 144893214-(2,5,6,6-Tetramethylcyclohex-1-en-1-yl)butan-2-one

Product 1

HCID 70926291HCID 70926291, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 4-(2,5,6,6-tetramethyl-cyclohex-1-enyl)-butan-2-one (10 g, 0.05 mol, commercially available at IFF), formamidine acetate (26 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-[2-(2,5,6,6-tetramethyl-cyclohex-1-enyl)-ethyl]-pyrimidine (˜10 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-6bc1dfd5cae346d4adb0f819f6997ce6
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

Loading…