Hydrochloric Acid → 2-(4-{4-[(2-Aminopyrimidin-4-yl)amino]-2-fluorophenoxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol
Reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][CH:14]=[C:15]([CH2:16][CH2:17][OH:18])[C:8]=23)=[C:4]([F:21])[CH:3]=1.Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[N:24]=1.Cl.[OH-].[Na+]>O>[NH2:29][C:25]1[N:26]=[C:27]([NH:1][C:2]2[CH:20]=[CH:19][C:5]([O:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[NH:13][CH:14]=[C:15]([CH2:16][CH2:17][OH:18])[C:8]=34)=[C:4]([F:21])[CH:3]=2)[CH:28]=[CH:23][N:24]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
135 mg (0.47 mmol) of 2-[4-(4-amino-2-fluorophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanol and 79 mg (0.61 mmol) of 4-chloropyrimidine-2-amine are suspended in 6 ml of water. 0.6 ml (0.6 mmol) of 1N hydrochloric acid is added, and the mixture is heated at reflux overnight. Using 1N aqueous sodium hydroxide solution, the suspension is adjusted to pH 10, resulting in the precipitation of crystals. The crystals are filtered off with suction, washed with water and purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 10:1).
Workup
- temperaturethe mixture is heated
- temperatureat reflux overnight
- customresulting in the precipitation of crystals
- filtrationThe crystals are filtered off with suction
- washwashed with water
- custompurified by column chromatography on silica gel (mobile phase: dichloromethane/methanol (7N ammonia) 100:1 to 10:1)
Sources & evidence
- ORD record
- ord-ab288ecfa6fc4cea9efb44e887cacaa9
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329716B2
Reaction notes
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