1H-Indol-2-ylboronic acid → N-((2-(1H-indol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-N-methylacetamide

HRID 2098701Notes

Reaction equation

HRID 2098701 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH3:16])[C:13](=[O:15])[CH3:14])=[CH:8][C:6]=2[N:7]=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1B(O)O>>[NH:23]1[C:31]2[C:26](=[C:27]([C:2]3[N:3]=[C:4]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:5]4[S:10][C:9]([CH2:11][N:12]([CH3:16])[C:13](=[O:15])[CH3:14])=[CH:8][C:6]=4[N:7]=3)[CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1

Participants

3

Reactant 2

HCID 225673581H-Indol-2-ylboronic acidHCID 59829246HCID 59829246, compound

Product 1

HCID 59593079N-((2-(1H-indol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)-N-methylacetamide

Procedure

N-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-methyl-acetamide was reacted with indole boronic acid in general procedure A. Purification on silica yielded 193. NMR: 400MHz; CDCl3 2.10, 2.18 (3H,s,2 rotamers); 3.00 (3H,s); 3.84 (4H,m); 4.00 (4H,m); 4.73, 4.77 (2H,s,2 rotamers); 7.26 (2H,m); 7.33 (1H,s); 7.42 (1H,m); 7.48 (1H,s); 8.13 (1H,m); 8.21 (1H,br s). MS: (ESI+):M+H(422)

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-4d0f602448df4556914261f134e26c12
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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