Hydrazine → 2-Ethyl-5-fluoro-4-hydrazino-6-(4-methyl-1-piperazinyl)pyrimidine
Reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[C:4]([CH2:10][CH3:11])[N:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.[NH2:28][NH2:29]>C(Cl)Cl.CO.O1CCOCC1>[CH2:10]([C:4]1[N:5]=[C:6]([NH:28][NH2:29])[C:7]([F:8])=[C:2]([N:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)[N:3]=1)[CH3:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To an ice-cold solution of 1,4-dioxane (10 mL) and MeOH (2 mL) was added 4,6-dichloro-2-ethyl-5-fluoropyrimidine (1.0 g, 5.13 mmol), N-methylpiperazine (626 uL, 5.64 mmol) and DIPEA (1.97 mL, 12.4 mmol) sequentially. The solution was then stirred at room temperature for 2 h. After the reaction was complete, anhydrous hydrazine (1.29 mL, 99 mmol) was added. The resulting suspension was heated at 90° C. in a oil bath for 2 h until the intermediate was consumed. Evaporation of the solvent gave a light yellow solid. The solid was dissolved in CH2Cl2 (100 mL) and washed with 1 N HCl. The aqueous phase was back-extracted with DCM (50 mL). The combined organic layers were dried over anhydrous Na2SO4. Evaporation of the solvent gave a light yellow residue as the desired product (890 mg, 69%).
Workup
- temperatureThe resulting suspension was heated at 90° C. in a oil bath for 2 h until the intermediate
- customwas consumed
- customEvaporation of the solvent
- customgave a light yellow solid
- washwashed with 1 N HCl
- extractionThe aqueous phase was back-extracted with DCM (50 mL)
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-ebbfc271b36c41e0be184b911abd6bae
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893056B2
Reaction notes
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