N,N-Dimethylaniline → 4-Chloro-3-(2-chloroethyl)-8-mesityl-2,6-dimethylimidazo[1,5-a]pyrimidine
Reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:5]([CH3:24])=[N:6][C:7]2[N:8]([C:11]([CH3:23])=[N:12][C:13]=2[C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])[C:9]=1O.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:36])=O>>[Cl:36][C:9]1[N:8]2[C:11]([CH3:23])=[N:12][C:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])=[C:7]2[N:6]=[C:5]([CH3:24])[C:4]=1[CH2:3][CH2:2][Cl:1]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
A solution of 3-(2-chloroethyl)-8-mesityl-2,6-dimethylimidazo[1,5-a]pyrimidin-4-ol (200 mg, 0.58 mmol) and N,N-dimethylaniline (0.3 mL) in phosphorus oxychloride (3 mL) was heated under reflux for six hours. After evaporating, 3-aminopentane (2 mL) was added to a solution of the residue in acetonitrile (5 mL), followed by stirring at 80° C. for three hours. Water was added, and the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10-20% ethyl acetate/hexane), to give the title compound (139 mg) as pale yellow crystals.
Workup
- temperatureunder reflux for six hours
- customAfter evaporating
- addition3-aminopentane (2 mL) was added to a solution of the residue in acetonitrile (5 mL)
- additionWater was added
- extractionthe mixture was extracted with ethyl acetate
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
- customThe residue was purified by silica gel column chromatography (10-20% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-0d48a87798ac456396c7b7f44636801b
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06951865B2
Reaction notes
Loading…