Hydrochloric Acid → N4-{3-Fluoro-4-[(1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)amino]phenyl}-6-pyridin-4-ylpyrimidine-2,4-diamine

HRID 2240267Notes

Reaction equation

HRID 2240267 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]([CH3:19])[CH:17]=[CH:18][C:11]=12.Cl[C:21]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)[N:24]=[C:23]([NH2:33])[N:22]=1.Cl.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:21]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[N:24]=[C:23]([NH2:33])[N:22]=2)[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16]([CH3:19])[CH:17]=[CH:18][C:11]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 223242864-Chloro-6-(pyridin-4-yl)pyrimidin-2-amineHCID 593050222-Fluoro-N1-(1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzene-1,4-diamine

Product 1

HCID 11510153N4-{3-Fluoro-4-[(1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)amino]phenyl}-6-pyridin-4-ylpyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 mg (0.78 mmol) of 2-fluoro-N1-(1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzene-1,4-diamine and 169 mg (0.82 mmol) of 4-chloro-6-pyridin-4-ylpyrimidine-2-amine are suspended in 5 ml of water. 84 μl (1.01 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-34679603a09a442c9d8cde17f9e3a7b0
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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