Hydrochloric Acid → N4-[3-Fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)phenyl]-6-pyridin-4-ylpyrimidine-2,4-diamine
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16](COCC[Si](C)(C)C)[CH:17]=[CH:18][C:11]=12.Cl[C:28]1[CH:33]=[C:32]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)[N:31]=[C:30]([NH2:40])[N:29]=1.Cl.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:28]2[CH:33]=[C:32]([C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[N:31]=[C:30]([NH2:40])[N:29]=2)[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[CH:18][C:11]=12Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
70 mg (0.19 mmol) of 2-fluoro-N1-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-yl)benzene-1,4-diamine and 41 mg (0.20 mmol) of 4-chloro-6-pyridin-4-ylpyrimidine-2-amine are suspended in 2.5 ml of water. 27 μl (0.28 mmol) of a 37% strength hydrochloric acid solution are then added, and the mixture is heated under reflux overnight. Using 1N aqueous sodium hydroxide solution, the suspension is then adjusted to pH 10, resulting in the precipitation of crystals. The solid is filtered off, washed with a little water and then dissolved in DMSO and purified by preparative RP-HPLC.
Workup
- temperaturethe mixture is heated
- temperatureunder reflux overnight
- customresulting in the precipitation of crystals
- filtrationThe solid is filtered off
- washwashed with a little water
- dissolutiondissolved in DMSO
- custompurified by preparative RP-HPLC
Sources & evidence
- ORD record
- ord-5cc0206e89cc402f8475de9689c0b35f
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723347B2
Reaction notes
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