Hydrazine hydrate (1:1) → 4-Hydrazinyl-2-methoxypyrimidine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[N:3]=1.O.[NH2:11][NH2:12]>CCO>[NH:11]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[N:3]=1)[NH2:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To a stirred solution of 4-chloro-2-methoxypyrimidine (5.7 g, 39.4 mmol) in EtOH (100 mL) under Ar was added hydrazine hydrate (3.83 mL, 79 mmol) and the reaction mixture was heated up and stirred at 85° C. for 1 hr. Volatiles were removed under reduced pressure and the resulting crude material was purified by silica gel column chromatography (CH2Cl2/MeOH/1-5%/NH3 1%) to afford the title product (4.40 g, 31.4 mmol, 80% yield) as white solid. ESI-MS: 141 [M+H]+ (LC-MS 2); Rf=0.47 (CH2Cl2/MeOH 9:1).
Workup
- temperaturethe reaction mixture was heated up
- customVolatiles were removed under reduced pressure
- customthe resulting crude material was purified by silica gel column chromatography (CH2Cl2/MeOH/1-5%/NH3 1%)
Sources & evidence
- ORD record
- ord-7b35b626b69f4237b6a0532709bce0b4
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975417B2
Reaction notes
Loading…