N,N-Dimethylaniline → N-Butyl-N-(6-(4-chlorobutyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)amine
Reaction equation
P(Cl)(Cl)([Cl:3])=O.C[N:7](C)[C:8]1C=C[CH:11]=[CH:10][CH:9]=1.C([C:19]1[N:24]2[N:25]=[C:26]([CH3:37])[C:27]([C:28]3[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=3[CH3:36])=[C:23]2[N:22]=[C:21]([CH3:38])[C:20]=1[CH2:39][CH2:40][CH2:41][CH2:42]O)CCC.C(=O)([O-])[O-].[K+].[K+]>>[CH2:8]([NH:7][C:20]1([CH2:39][CH2:40][CH2:41][CH2:42][Cl:3])[CH2:19][N:24]2[N:25]=[C:26]([CH3:37])[C:27]([C:28]3[C:29]([CH3:36])=[CH:30][C:31]([CH3:35])=[CH:32][C:33]=3[CH3:34])=[C:23]2[N:22]=[C:21]1[CH3:38])[CH2:9][CH2:10][CH3:11]Participants
5
Procedure
Phosphorus oxychloride (11.3 g) and N,N-dimethylaniline (3 droplets) were added to 4-(7-(butyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)-1-butanol (320 mg, 0.78 mmol), followed by heating under reflux for 0.5 hour. After the reaction, the mixture was treated with ice-water, neutralized with potassium carbonate, extracted with ethyl acetate, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10-15% ethyl acetate/hexane), to give the title compound (254 mg) as a pale yellow oil.
Workup
- temperatureby heating
- temperatureunder reflux for 0.5 hour
- customAfter the reaction
- extractionextracted with ethyl acetate
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
- customThe residue was purified by silica gel column chromatography (10-15% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-a5bf72ebbeda4aea8c553b798c0d59c0
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06927221B2
Reaction notes
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