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Hydrochloric Acid → N4-[3-Fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)phenyl]-6-pyridin-4-ylpyrimidine-2,4-diamine

HRID 2240262
Notes
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Reaction equation

HRID 2240262 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]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 223242864-Chloro-6-(pyridin-4-yl)pyrimidin-2-amineHCID 593049942-Fluoro-N-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)benzene-1,4-diamine

Product 1

HCID 59305003N4-[3-Fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)phenyl]-6-pyridin-4-ylpyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. customresulting in the precipitation of crystals
  4. filtrationThe solid is filtered off
  5. washwashed with a little water
  6. dissolutiondissolved in DMSO
  7. custompurified by preparative RP-HPLC

Sources & evidence

ORD record
ord-5cc0206e89cc402f8475de9689c0b35f
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07723347B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes