Potassium Carbonate → HCID 70981469, compound

HRID 1409432Notes

Reaction equation

HRID 1409432 reaction equation
[CH:1]([C:4]1[NH:5][CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:8]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:19][Si:20]([CH2:23][CH2:24][O:25][CH2:26]Cl)([CH3:22])[CH3:21]>CN(C=O)C.O>[CH:1]([C:4]1[N:5]([CH2:26][O:25][CH2:24][CH2:23][Si:20]([CH3:22])([CH3:21])[CH3:19])[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178498880HCID 178498880, compound

Product 1

HCID 70981469HCID 70981469, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Into a flask containing a solution of methyl 2-isopropyl-1H-imidazole-4-carboxylate (2.7 g, 16.1 mmol) in DMF (20 ml), K2CO3 (5.5 g, 40.2 mmol) and SEM-Cl (3.5 g, 21.0 mmol) were added. The resulting mixture was heated at 80° C. for 18 h. The reaction mixture was diluted with H2O and extracted with EtOAc. The product was purified with flash chromatography. Yield 830 mg. 1H-NMR (400 MHz; CDCl3): δ 0.04 (s, 9H), 0.85-0.89 (m, 2H), 1.28 (d, 6H), 3.15-3.20 (m, 1H), 3.57 (t, 2H), 3.83 (s, 3H), 5.74 (s, 2H), 7.69 (s, 1H).

Workup

  1. additionwere added
  2. extractionextracted with EtOAc
  3. customThe product was purified with flash chromatography

Sources & evidence

ORD record
ord-46d8d93f637a4999847378fe4f864a7b
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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