Hydrochloric Acid → 6-Chloro-N4-{4-[(3-ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}pyrimidine-2,4-diamine

HRID 2192186Notes

Reaction equation

HRID 2192186 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[F:20])[NH:5][CH:4]=1)[CH3:2].[Cl:21][C:22]1[CH:27]=[C:26](Cl)[N:25]=[C:24]([NH2:29])[N:23]=1.Cl.[OH-].[Na+]>O>[Cl:21][C:22]1[N:23]=[C:24]([NH2:29])[N:25]=[C:26]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([O:12][C:10]3[CH:9]=[CH:8][N:7]=[C:6]4[NH:5][CH:4]=[C:3]([CH2:1][CH3:2])[C:11]=34)=[C:14]([F:20])[CH:15]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 597410004-[(3-Ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline

Product 1

HCID 116398946-Chloro-N4-{4-[(3-ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 mg (0.18 mmol) of 4-[(3-ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline and 32 mg (0.19 mmol) of 4,6-dichloropyrimidine-2-amine are suspended in 5 ml of water. 27 μl of 37% strength hydrochloric acid are added, and the mixture is heated at reflux overnight. Using 1N aqueous sodium hydroxide solution, the pH is then adjusted to 10, resulting in the precipitation of crystals. The crystals are filtered off with suction and purified by preparative HPLC.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. customresulting in the precipitation of crystals
  4. filtrationThe crystals are filtered off with suction
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d058f112d172470b8e92dd04427dcc82
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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