(1-Benzothiophen-3-yl)boronic acid → 2-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine

HRID 1422503Notes

Reaction equation

HRID 1422503 reaction equation
[Cl:1][C:2]1[N:10]=[C:9](I)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13].[S:15]1[CH:19]=[C:18](B(O)O)[C:17]2[CH:23]=[CH:24][CH:25]=[CH:26][C:16]1=2>>[S:15]1[CH:19]=[C:18]([C:9]2[N:8]=[C:7]3[C:3]([N:4]=[CH:5][N:6]3[CH:12]([CH3:14])[CH3:13])=[C:2]([Cl:1])[N:10]=2)[C:17]2[CH:23]=[CH:24][CH:25]=[CH:26][C:16]1=2

Participants

3

Reactant 2

HCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 65389046-Chloro-2-iodo-9-isopropyl-9H-purine

Product 1

HCID 594089202-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine

Procedure

Following the procedure of Example 15d, 6-chloro-2-iodo-9-isopropyl-9H-purine (3.31 g, 0.0103 mol) was reacted with benzo[b]thiophen-3-ylboronic acid. The crude product was purified by silica gel chromatography (20 to 50% ethyl acetate in hexane) to afford the title compound as a solid. MS m/z 329.0 (M+1). 1H NMR (400 MHz, DMSO-d6): δ=9.15 (d, 1H), 8.85 (s, 2H), 8.17 (d, 1H), 7.62 (t, 1H), 7.53 (t, 1H), 5.06 (m, 1H), 1.71 (d, 6H).

Workup

  1. customThe crude product was purified by silica gel chromatography (20 to 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8a6c3a879baf49debfd4d9fdbcb919c6
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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