Potassium Carbonate → phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamate

HRID 929995Notes

Reaction equation

HRID 929995 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([CH3:11])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]([CH3:11])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 27352873-tert-Butyl-1-methyl-1H-pyrazol-5-amine

Product 1

HCID 46196890phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamateYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-tert-butyl-1-methyl-1H-pyrazol-5-amine (0.75 g, 9.8 mmol) and potassium carbonate (1.76 g, 12.7 mmol) in THF (20 mL) at 0° C. was added dropwise phenyl chloroformate (0.7 mL, 10.8 mmol). The mixture was stirred at rt for 16 h. The mixture was then filtered through celite and solvent was removed under reduced pressure. The crude residue was purified by silica gel flash chromatography, eluting with 0% to 100% EtOAc in hexanes, to afford phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamate (1.05 g, 39% yield). LCMS (ESI) m/z 348 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.11 (br s, 1H), 7.45-7.40 (m, 2H), 7.29-7.21 (m, 3H), 6.04 (s, 1H), 3.58 (s, 3H), 1.20 (s, 9H).

Workup

  1. filtrationThe mixture was then filtered through celite and solvent
  2. customwas removed under reduced pressure
  3. customThe crude residue was purified by silica gel flash chromatography
  4. washeluting with 0% to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-c4cb4fa7029c44b7a5dc6648026e64ce
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Reaction notes

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