Lithium Hydroxide → HCID 57990333, compound

HRID 2281493Notes

Reaction equation

HRID 2281493 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-72944bad118c4e0f8d4d3ac7b92986fe
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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