Sodium borohydride → HCID 24854824, compound

HRID 2189317Notes

Reaction equation

HRID 2189317 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[CH:19][C:20]4[CH:25]=[C:24]([CH:26]=[O:27])[N:23]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:21]=4[N:22]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[CH2:29]([CH:28]([N:23]1[C:21]2[N:22]=[C:17]([NH:16][C:13]3[CH:12]=[CH:11][C:10]([N:7]4[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]4)=[CH:15][CH:14]=3)[N:18]=[CH:19][C:20]=2[CH:25]=[C:24]1[CH2:26][OH:27])[CH2:31][CH3:32])[CH3:30]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23624284HCID 23624284, compound

Product 1

HCID 24854824HCID 24854824, compoundYield 74.7%

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-carbaldehyde (20 mg, 0.046 mmol) in MeOH (1 mL) is added NaBH4 (3.5 mg, 0.092 mmol). The reaction mixture is stirred for 1 h and concentrated in vacuo. The residue is purified by preparative HPLC to give 15 mg of 1-(4-{4-[7-(1-ethyl-propyl)-6-hydroxymethyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanone.

Workup

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

Sources & evidence

ORD record
ord-2be61b04b216415d84370f3167013019
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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