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

HRID 2192181Notes

Reaction equation

HRID 2192181 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]=[C:18]([CH3:19])[C:11]=12)[NH2:5].[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[C:23]([NH2:28])[N:22]=1.Cl.[OH-].[Na+]>O>[Cl:20][C:21]1[N:22]=[C:23]([NH2:28])[N:24]=[C:25]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]4[NH:16][CH:17]=[C:18]([CH3:19])[C:11]=34)=[C:2]([F:1])[CH:3]=2)[CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 179793083-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline

Product 1

HCID 116609846-Chloro-N4-{3-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

35 mg (0.14 mmol) of 3-fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]aniline and 24.5 mg (0.15 mmol) of 4,6-dichloropyrimidine-2-amine are suspended in 2.5 ml of water. 17 μl (0.18 mmol) of 37% strength hydrochloric acid are added, and the mixture is heated at reflux overnight. Using 1N aqueous sodium hydroxide solution, the pH is adjusted to 10, resulting in the precipitation of crystals. The crystals are filtered off with suction and purified by column chromatography on silica gel (mobile phase: dichloromethane:methanol (7N ammonia) 100:5).

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 column chromatography on silica gel (mobile phase: dichloromethane:methanol (7N ammonia) 100:5)

Sources & evidence

ORD record
ord-b97f13b8cde14589be4e7a67a28a6c17
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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