N-bromobutanimide → (3-Bromo-1H-indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine

HRID 2297815Notes

Reaction equation

HRID 2297815 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]4[S:19][C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Br:26]N1C(=O)CCC1=O>C(Cl)Cl>[Br:26][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([NH:10][C:11]3[C:12]4[S:19][C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:5]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 9884465(1H-Indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine

Product 1

HCID 18382896(3-Bromo-1H-indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amineYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1H-Indol-5-yl)-(6-phenyl-thieno[3,2-d]pyrimidin-4-yl)-amine (150 mg, 0.438 mmol) in methylene chloride was added N-bromosuccinimide (86 mg, 0.482 mmol). The reaction mixture was stirred for 2 days at room temperature and then concentrated in vacuo. The orange residue was chromatographed by preparative reverse-phase HPLC using a 200 nM acetate buffer and acetonitrile gradient to afford pure product (17% yield). RP18-HPLC RT: 6.377 minutes; API MS: 371.2 (M+1); MP: 201-203° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe orange residue was chromatographed by preparative reverse-phase

Sources & evidence

ORD record
ord-e7f80e18f79340eaa636b17131ea14b1
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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