Sodium Hydroxide → 4-(5-bromo-1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-amine
Reaction equation
[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][N:11]([NH:13]C(=O)OC)[CH:12]=1.[OH-].[Na+]>>[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][N:11]([NH2:13])[CH:12]=1Participants
3
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
- temperatureAfter cooling
- extractionthe aqueous mixture was extracted five times with 2-butanol
- dry with materialthe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b712d6e2610e4c79b42b754cef9a223e
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598155B2
Reaction notes
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