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

HRID 16445Notes

Reaction equation

HRID 16445 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O: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]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:23]=[C:22]([NH2:33])[N:21]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O.CN(C)C=O.C(OCC)(=O)C>[F:32][C:29]1[CH:28]=[CH:27][C:26]([C:24]2[N:23]=[C:22]([NH2:33])[N:21]=[C:20]([NH:5][C:4]3[CH:6]=[CH:7][C:8]([O: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:3]=3)[CH:25]=2)=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 112183534-Chloro-6-(4-fluorophenyl)pyrimidin-2-amineHCID 160379654-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline

Product 1

HCID 587332456-(4-Fluorophenyl)-N4-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-pyrimidine-2,4-diamine

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

36 mg (0.15 mmol) of 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline (from example XIX) and 38.5 mg (0.15 mmol) of 4-chloro-6-(4-fluorophenyl)pyrimidine-2-amine (from example LIX) are suspended in 1.5 ml of water, and 0.1 ml of 2 molar hydrochloric acid is added. The mixture is heated under reflux overnight. Ethyl acetate and a few drops of dimethylformamide are then added. The mixture is made alkaline using saturated sodium carbonate solution, the organic phase is separated off and the solvent is removed under reduced pressure. The product is purified by preparative HPLC.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux overnight
  3. customthe organic phase is separated off
  4. customthe solvent is removed under reduced pressure
  5. customThe product is purified by preparative HPLC

Sources & evidence

ORD record
ord-6a13486060884f89b5d33e9e22cce4c7
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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