Hydrochloric Acid → 2-(4-{4-[(2-Amino-6-chloropyrimidin-4-yl)amino]-2-fluorophenoxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

HRID 2192188Notes

Reaction equation

HRID 2192188 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][CH:14]=[C:15]([CH2:16][CH2:17][OH:18])[C:8]=23)=[C:4]([F:21])[CH:3]=1.[Cl:22][C:23]1[CH:28]=[C:27](Cl)[N:26]=[C:25]([NH2:30])[N:24]=1.Cl.[OH-].[Na+]>O>[NH2:30][C:25]1[N:26]=[C:27]([NH:1][C:2]2[CH:20]=[CH:19][C:5]([O:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[NH:13][CH:14]=[C:15]([CH2:16][CH2:17][OH:18])[C:8]=34)=[C:4]([F:21])[CH:3]=2)[CH:28]=[C:23]([Cl:22])[N:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 210815442-[4-(4-Amino-2-fluorophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanol

Product 1

HCID 116113682-(4-{4-[(2-Amino-6-chloropyrimidin-4-yl)amino]-2-fluorophenoxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

56 mg (0.17 mmol) of 2-[4-(4-amino-2-fluorophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanol and 30 mg (0.18 mmol) of 4,6-dichloropyrimidine-2-amine are suspended in 5 ml of water. 25 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 mixture is concentrated and filtered through silica gel. The product is purified by preparative HPLC.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. customresulting in the precipitation of crystals
  4. concentrationThe mixture is concentrated
  5. filtrationfiltered through silica gel
  6. customThe product is purified by preparative HPLC

Sources & evidence

ORD record
ord-0fd108df6e8a457aabf112fdd3166f23
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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