Tolylboronic acid → (1H-Indol-5-yl)-(6-p-tolyl-thieno[3,2-d]pyrimidin-4-yl)-amine

HRID 2297758Notes

Reaction equation

HRID 2297758 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[S:20][C:19]2[C:18]([NH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[NH:27][CH:26]=[CH:25]4)=[N:17][CH:16]=[N:15][C:14]=2[CH:13]=1>>[NH:27]1[C:28]2[C:24](=[CH:23][C:22]([NH:21][C:18]3[C:19]4[S:20][C:12]([C:5]5[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=5)=[CH:13][C:14]=4[N:15]=[CH:16][N:17]=3)=[CH:30][CH:29]=2)[CH:25]=[CH:26]1

Participants

3

Reactant 2

HCID 79799Tolylboronic acidHCID 18383051(6-Bromo-thieno[3,2-d]pyrimidin-4-yl)-(1H-indol-5-yl)-amine

Product 1

HCID 9798795(1H-Indol-5-yl)-(6-p-tolyl-thieno[3,2-d]pyrimidin-4-yl)-amine

Procedure

The title compound was prepared from p-methylbenzeneboronic 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 11.1 (s, 1H), 9.50 (s, 1H), 8.41 (s, 1H), 7.71 (d, 2H), 7.59 (s, 2H), 7.24 (m, 5H), 6.38 (s, 1H), 2.28 (s, 3H). M.P. 200-220° C.; LC-MS: 357 (MH+); HPLC RT: 4.57 minutes.

Sources & evidence

ORD record
ord-98291b74b15e4d44b587806ad954b66a
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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