3-Formylphenylboronic acid → HCID 86619250, compound

HRID 2403370Notes

Reaction equation

HRID 2403370 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[CH:25]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1)=[O:26]>>[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:9]2[S:10][C:5]3[C:4]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:3][C:2]([C:31]4[CH:32]=[C:27]([CH:28]=[CH:29][CH:30]=4)[CH:25]=[O:26])=[N:7][C:6]=3[CH:8]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 27343563-Formylphenylboronic acidHCID 574203384-(2-Chloro-6-((4-methylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86619250HCID 86619250, compound

Procedure

2-Chloro-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine was reacted with 3-formyl phenyl boronic acid in General Procedure A. Purification on silica yielded 3-[6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl]-benzaldehyde. This was then treated with sodium borohydride in methanol to give the desired compound.

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-02208028810249139cbf454a45f3abc4
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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