Sodium Hydroxide → 4-(5-bromo-1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-amine

HRID 1498048Notes

Reaction equation

HRID 1498048 reaction equation
COC(=O)[NH:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][N:13]([CH3:16])[C:14]=2[Br:15])[N:7]=[CH:6]1.[OH-].[Na+]>>[Br:15][C:14]1[N:13]([CH3:16])[N:12]=[CH:11][C:10]=1[C:8]1[N:7]=[CH:6][N:5]([NH2:4])[CH:9]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86669722methyl[4-(5-bromo-1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl]carbamate

Product 1

HCID 681819934-(5-bromo-1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-amine

Conditions

Temperature
100 °C

Procedure

A mixture of methyl[4-(5-bromo-1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl]carbamate (400 mg, 1.33 mmol) and aqueous sodium hydroxide solution (1 M, 1.33 mL, 1.33 mmol) was heated at 100° C. for 18 hours. After cooling, the aqueous mixture was extracted five times with 2-butanol, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide the product as a beige solid. Yield: 310 mg, 1.28 mmol, 96%. 1H NMR (400 MHz, CD3OD) δ 3.89 (s, 3H), 7.46 (d, J=1.2 Hz, 1H), 7.61 (d, J=1.3 Hz, 1H), 7.82 (s, 1H).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous mixture was extracted five times with 2-butanol
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-889fbef86cd14ac4aeacfc3ae25a6c18
Source dataset
uspto-grants-2015_12
Patent number
US09200000B2

Reaction notes

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