Hydrochloric Acid → 4-{4-[(2-Aminopyrimidin-4-yl)amino]-2-fluorobenzyl}-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 2240271Notes

Reaction equation

HRID 2240271 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][CH:14]=[C:15]([C:16]#[N:17])[C:8]=23)=[C:4]([F:20])[CH:3]=1.Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH2:28])[N:23]=1.Cl.[OH-].[Na+]>O.CO.C(O)C>[NH2:28][C:24]1[N:25]=[C:26]([NH:1][C:2]2[CH:19]=[CH:18][C:5]([CH2:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[NH:13][CH:14]=[C:15]([C:16]#[N:17])[C:8]=34)=[C:4]([F:20])[CH:3]=2)[CH:27]=[CH:22][N:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2233322-Amino-4-chloropyrimidineHCID 593049784-(4-Amino-2-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Product 1

HCID 593050194-{4-[(2-Aminopyrimidin-4-yl)amino]-2-fluorobenzyl}-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

120 mg (0.45 mmol) of 4-(4-amino-2-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile and 64 mg (0.50 mmol) of 4-chloropyrimidine-2-amine are suspended in 4 ml of water, 2 ml of ethanol and 0.23 ml of 4N hydrochloric acid. The reaction mixture is heated at reflux for 2 hours. After cooling, the mixture is made alkaline using dilute aqueous sodium hydroxide solution, a little methanol is added, the mixture is extracted with ethyl acetate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC. This gives crystals.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with ethyl acetate
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-c6c9deb4542e448984c26726e7c59de9
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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