Lithium Hydroxide → HCID 57990333, compound

HRID 2381719Notes

Reaction equation

HRID 2381719 reaction equation
[NH2:1][C:2]1[C:3]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[CH:23][NH:22][C:4]=2[N:5]=[C:6]([NH:8][C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15]CCCC)=[O:14])=[CH:11][CH:10]=2)[N:7]=1.[Li+].[OH-]>C1COCC1>[NH2:1][C:2]1[C:3]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[CH:23][NH:22][C:4]=2[N:5]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:20][CH:21]=2)[N:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57990405HCID 57990405, compound

Product 1

HCID 57990333HCID 57990333, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of butyl 4-(4-amino-5-(pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzoate (137 mg, 0.340 mmol) in THF (3 mL), aq. 1N LiOH (2.0 mL, 2.0 mmol) was added. The mixture was stirred at room temperature for 20 h. It was concentrated in vacuo. The residue was acidified with HOAc (2 mL), then was purified by HPLC to give the titled compound (55 mg). MS 347.2 (M+H); UV 203.8, 306.7 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. customwas purified by HPLC

Sources & evidence

ORD record
ord-8d12104b75aa4cf7b8c2f5e6317e2b87
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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