Hydrazine → 2-n-Butoxy-4-hydrazino-6-(morpholin-4-yl)pyrimidine
Reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[C:10](Cl)[CH:9]=[C:8]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:19][NH2:20]>O1CCOCC1>[CH2:1]([O:5][C:6]1[N:11]=[C:10]([NH:19][NH2:20])[CH:9]=[C:8]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:7]=1)[CH2:2][CH2:3][CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To a solution of 2-n-butoxy-4-chloro-6-(morpholin-4-yl)pyrimidine (1.38 g, 5.1 mmol) in dioxane (50 ml), anhydrous hydrazine (1.6 mL, 50 mmol) was added. The obtained reaction mixture was heated to 95° C., and stirred for 12 h under N2. After cooling to room temperature, the reaction mixture was quenched with ice-brine and extracted with EtOAc (200 mL). The organic extract was washed with brine, water, and dried over Na2SO4. The solvent was removed under reduced pressure. The crude residue was recrystallized from methanol to obtain 2-n-butoxy-4-hydrazino-6-(morpholin-4-yl)pyrimidine as white crystals (1.10 g, 81%).
Workup
- customThe obtained reaction mixture
- temperatureAfter cooling to room temperature
- customthe reaction mixture was quenched with ice-brine
- extractionextracted with EtOAc (200 mL)
- extractionThe organic extract
- washwas washed with brine, water
- dry with materialdried over Na2SO4
- customThe solvent was removed under reduced pressure
- customThe crude residue was recrystallized from methanol
Sources & evidence
- ORD record
- ord-4a3f0645526e4fbd82e6856441367ec4
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465725B2
Reaction notes
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