Hydrazine hydrate (1:1) → 4-Hydrazinyl-6-(methylthio)pyrimidine
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([S:8][CH3:9])[N:5]=[CH:4][N:3]=1.O.[NH2:11][NH2:12]>CC(O)C>[CH3:9][S:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:11][NH2:12])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 4-Chloro-6-methylsulfanyl-pyrimidine (1.1 g, 6.85 mmol), hydrazine monohydrate (1.2 g, 23.5 mmol), and 2-propanol (10 mL) is heated to 90° C. for 4 hours. The reaction mixture is then cooled to room temperature, concentrated, triturated with water, and filtered. The undissolved solid is washed with water, air-dried to give (6-Methylsulfanyl-pyrimidin-4-yl)-hydrazine as light yellow solid: 1H NMR 400 MHz (d6-DMSO) δ 8.29 (s, 1H), 8.16 (s, 1H), 6.55 (s, 1H), 4.34 (s, 2H), 2.43 (s, 3H); MS m/z 157.05 (M+1).
Workup
- temperatureThe reaction mixture is then cooled to room temperature
- concentrationconcentrated
- customtriturated with water
- filtrationfiltered
- washThe undissolved solid is washed with water
- customair-dried
Sources & evidence
- ORD record
- ord-c0c0e69b57914f5c9f5f0fa4353d5036
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202876B2
Reaction notes
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