Water → HCID 57471658, compound

HRID 887368Notes

Reaction equation

HRID 887368 reaction equation
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)[C:8]([C:37]#[N:38])=[CH:7][N:6]=1)([CH3:3])[CH3:2].O.[Li+].[OH-]>C1COCC1>[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:18]=3)[NH:13][CH:12]=2)[C:8]([C:37]#[N:38])=[CH:7][N:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 686678792-(isopropylamino)-4-(5-(phenylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

Product 1

HCID 57471658HCID 57471658, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(isopropylamino)-4-(5-(phenylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile (0.083 g, 0.158 mmol) was stirred in THF (7 mL) and water (1.5 mL) and treated with LiOH.H20 (0.066 g, 1.60 mmol, 10.0 Eq) and allowed to stir at room temperature for 16 hours. The reaction mixture was concentrated and purified by column chromatography (50% EtOAc/Petroleum ether) to yield the product as a yellow solid (29 mg, 50%)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography (50% EtOAc/Petroleum ether)

Sources & evidence

ORD record
ord-254d7df3829e42298741bb9d471d12fe
Source dataset
uspto-grants-2012_08
Patent number
US08247421B2

Reaction notes

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