Lithium Hydroxide → 2-[4-(4-Acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

HRID 2189323Notes

Reaction equation

HRID 2189323 reaction equation
C[O:2][C:3]([C:5]1[N:29]([CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23]([C:26](=[O:28])[CH3:27])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-]>CO>[C:26]([N:23]1[CH2:22][CH2:21][N:20]([C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:10]3[N:11]=[CH:12][C:7]4[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[N:29]([CH:30]([CH2:31][CH3:32])[CH2:33][CH3:34])[C:8]=4[N:9]=3)=[CH:15][CH:16]=2)[CH2:25][CH2:24]1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 580159672-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Product 1

HCID 580159572-[4-(4-Acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acidYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid methyl ester (19 mg, 0.041 mmol) in MeOH (1.5 mL) is added 2 N LiOH aqueous solution (0.5 mL). The reaction mixture is stirred overnight and concentrated in vacuo. The residue is purified by preparative HPLC to give 13.6 mg of 2-[4-(4-Acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-a135f0e523bf4cb8aa19a8dce9428594
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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