(Pyrimidin-5-yl)boronic acid → HCID 58234043, compound

HRID 881303Notes

Reaction equation

HRID 881303 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[CH:10]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[S:8][C:6]=2[N:7]=1.[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1>>[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:9]2[S:8][C:6]3[N:7]=[C:2]([C:29]4[CH:30]=[N:25][CH:26]=[N:27][CH:28]=4)[N:3]=[C:4]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:5]=3[CH:10]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 56833947HCID 56833947, compound

Product 1

HCID 58234043HCID 58234043, compound

Procedure

2-Chloro-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[2,3-d]pyrimidine was reacted with pyrimidine-5-boronic acid in General Procedure A. Purification on silica yielded 169. NMR (CDCl3): 2.30 (3H, s, Me), 2.48-2.64 (8H, m, CH2), 3.71 (2H, s, CH2), 3.88-3.93 (4H, m, CH2), 3.98-4.03 (4H, m, CH2), 7.15 (1H, s, Ar), 9.21 (1H, s, Ar) and 9.62 (2H, s, Ar). MS: (ESI+): MH+ 412.33

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-d74a30e52af84ae88a165245bb4e4fca
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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