4-(Methylthio)phenylboronic acid → (1H-Indol-5-yl)-[6-(4-methylsulfanyl-phenyl)-thieno[3,2-d]pyrimidin-4-yl]-amine

HRID 2297761Notes

Reaction equation

HRID 2297761 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[S:21][C:20]2[C:19]([NH:22][C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[NH:28][CH:27]=[CH:26]4)=[N:18][CH:17]=[N:16][C:15]=2[CH:14]=1>>[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([NH:22][C:19]3[C:20]4[S:21][C:13]([C:6]5[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=5)=[CH:14][C:15]=4[N:16]=[CH:17][N:18]=3)=[CH:31][CH:30]=2)[CH:26]=[CH:27]1

Participants

3

Reactant 2

HCID 27339594-(Methylthio)phenylboronic acidHCID 18383051(6-Bromo-thieno[3,2-d]pyrimidin-4-yl)-(1H-indol-5-yl)-amine

Product 1

HCID 18382754(1H-Indol-5-yl)-[6-(4-methylsulfanyl-phenyl)-thieno[3,2-d]pyrimidin-4-yl]-amine

Procedure

The title compound was prepared from 4-(methylthio)benzeneboronic acid and (6-bromo-thieno[3,2-d]pyrimidin-4-yl)-(1H-indol-5-yl)-amine by a procedure analogous to example 2. 1H NMR (400 MHz, DMSO) d 11.4 (s, 1H), 11.2 (s, 1H), 8.82 (s, 1H), 7.76 (d, 2H), 7.76 (d, 2H), 7.61 (s, 2H), 7.51 (m, 2H), 7.35 d, 2H), 7.22 (d, 1H), 6.50 (s, 1H), 2.49 (s, 3H), M.P. 163-178° C.; LC-MS 389 (MH+); HPLC RT: 4.73 minutes.

Sources & evidence

ORD record
ord-b5453a17873c492e84fa5f5c4854cc68
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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