Diisopropylethylamine → HCID 86636952, compound
Reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:9][CH2:8][NH:7][C@H:6]([CH3:10])[CH2:5]1.C(N(CC)C(C)C)(C)C.[Cl:20][C:21]1[C:26]([F:27])=[C:25](Cl)[N:24]=[C:23]([CH3:29])[N:22]=1>ClCCl>[Cl:20][C:21]1[C:26]([F:27])=[C:25]([N:7]2[CH2:8][CH2:9][N:4]([CH3:3])[CH2:5][C@H:6]2[CH3:10])[N:24]=[C:23]([CH3:29])[N:22]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
To a solution of (3R)-1,3-dimethylpiperazine dihydrochloride (Example 63) (5.88 g, 31.4 mmol) in dichloromethane (126 mL) was added N,N-diisopropylethylamine (18.11 mL, 104 mmol), and 4,6-dichloro-5-fluoro-2-methylpyrimidine (5.69 g, 31.4 mmol). The solution was heated at 35° C. and stirred for 3 days. The solution was cooled to room temperature, diluted with DCM (100 mL), and washed with sat. aq. NaHCO3 (100 mL). The aqueous phase was extracted with a fresh portion of DCM (50 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude 4-chloro-6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine (9.60 g, >100% yield) as a brown oil that was used without further purification. LCMS: (M+H)+: 258.9.
Workup
- temperatureThe solution was cooled to room temperature
- washwashed with sat. aq. NaHCO3 (100 mL)
- extractionThe aqueous phase was extracted with a fresh portion of DCM (50 mL)
- dry with materialthe combined organic phase was dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-95ca18012bfe46068a161c298ea61efd
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893056B2
Reaction notes
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