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

HRID 2189324Notes

Reaction equation

HRID 2189324 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(=O)C)[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-]>C1COCC1>[CH2:31]([CH:30]([N:29]1[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)=[CH:18][CH:19]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[C:3]([OH:4])=[O:2])[CH2:33][CH3:34])[CH3:32]

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 580159967-(1-ethyl-propyl)-2-(4-piperazin-1-yl-phenylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acidYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (16 mg, 0.034 mmol) in THF (1.5 mL) is added 2 N LiOH aqueous solution (1 mL). The reaction mixture is stirred for 36 h and concentrated in vacuo. The residue is purified by preparative HPLC to give 9.4 mg of 7-(1-ethyl-propyl)-2-(4-piperazin-1-yl-phenylamino)-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-78a9455cf6d245cea4bcc5d5a2e0943e
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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