3-Formylphenylboronic acid → HCID 86619249, compound

HRID 2403364Notes

Reaction equation

HRID 2403364 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[CH:10]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]3)[S:8][C:6]=2[N:7]=1.[CH:28]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)=[O:29]>>[CH3:21][S:18]([N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:9]2[S:8][C:6]3[N:7]=[C:2]([C:34]4[CH:35]=[C:30]([CH:31]=[CH:32][CH:33]=4)[CH:28]=[O:29])[N:3]=[C:4]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[C:5]=3[CH:10]=2)[CH2:13][CH2:14]1)(=[O:20])=[O:19]

Participants

3

Reactant 2

HCID 27343563-Formylphenylboronic acidHCID 568339462-Chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[2,3-d]pyrimidine

Product 1

HCID 86619249HCID 86619249, compound

Procedure

2-Chloro-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[2,3-d]pyrimidine was reacted with 3-formylphenylboronic acid in General Procedure A to yield 3-[6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[2,3-d]pyrimidin-2-yl]-benzaldehyde. Treatment of this aldehyde with sodium borohydride (2.5 equivalents) in ethanol yielded the desired compound.

Sources & evidence

ORD record
ord-fb9ea441fa3e4d90a08560197243fbd7
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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