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Methanol → N4-[3-Fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)phenyl]-6-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 2240264
Notes
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Reaction equation

HRID 2240264 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[CH:18][C:11]=12)[NH2:5].Cl[C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:23]=[C:22]([NH2:30])[N:21]=1.[OH-].[Na+].CO>O.Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[N:23]=[C:22]([NH2:30])[N:21]=2)[CH:6]=[CH:7][C:8]=1[CH2:9][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

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 130869074-Chloro-6-(trifluoromethyl)pyrimidin-2-amineHCID 593050333-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline

Product 1

HCID 59305029N4-[3-Fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)phenyl]-6-(trifluoromethyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

32 mg (0.11 mmol) of 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline and 26 mg (0.12 mmol) of 4-chloro-6-(trifluoromethyl)pyrimidine-2-amine are suspended in 5 ml of water and 0.07 ml of 2N hydrochloric acid. The reaction mixture is heated at reflux for 20 hours. After cooling, the mixture is made alkaline using dilute aqueous sodium hydroxide solution, a little methanol is added and the mixture is extracted with ethyl acetate. The extract is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe extract is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-84a9ae195727482ba5a945629d9c773d
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