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

HRID 2240261
Notes
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Reaction equation

HRID 2240261 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][C:37]([F:40])=[CH:36][CH:35]=2)[N:31]=[C:30]([NH2:41])[N:29]=1.Cl.[OH-].[Na+]>O>[F:40][C:37]1[CH:36]=[CH:35][C:34]([C:32]2[N:31]=[C:30]([NH2:41])[N:29]=[C:28]([NH:8][C:6]3[CH:5]=[CH:4][C:3]([NH:9][C:10]4[CH:15]=[CH:14][N:13]=[C:12]5[NH:16][CH:17]=[CH:18][C:11]=45)=[C:2]([F:1])[CH:7]=3)[CH:33]=2)=[CH:39][CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 112183534-Chloro-6-(4-fluorophenyl)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 593049756-(4-Fluorophenyl)-N4-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)phenyl]pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 mg (0.27 mmol) of 2-fluoro-N1-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)benzene-1,4-diamine and 63 mg (0.28 mmol) of 4-chloro-6-(4-fluorophenyl)pyrimidine-2-amine are suspended in 3 ml of water. 39 μl (0.40 mmol) of a 37% strength hydrochloric acid solution are then added, and the mixture is heated under reflux overnight. After addition of a further 39 μl (0.40 mmol) of a 37% strength hydrochloric acid solution, the mixture is again reacted 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. customthe mixture is again reacted
  4. temperatureunder reflux overnight
  5. customresulting in the precipitation of crystals
  6. filtrationThe solid is filtered off
  7. washwashed with a little water
  8. dissolutiondissolved in DMSO
  9. custompurified by preparative RP-HPLC

Sources & evidence

ORD record
ord-1602cf236aca4247a7989579182d4c3a
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