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

HRID 2297754Notes

Reaction equation

HRID 2297754 reaction equation
[Br:1][C:2]1[S:10][C:9]2[C:8](Cl)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2>ClC(Cl)C.C(O)(C)(C)C>[Br:1][C:2]1[S:10][C:9]2[C:8]([NH:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][CH:17]=[CH:16]4)=[N:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 788675-AminoindoleHCID 183827966-Bromo-4-chlorothieno(3,2-d)pyrimidine

Product 1

HCID 18383051(6-Bromo-thieno[3,2-d]pyrimidin-4-yl)-(1H-indol-5-yl)-amineYield 121.7%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 6386tert-ButanolSolvent

Procedure

6-Bromo-4-chloro-thieno[3,2-d]pyrimidine (7.73 g, 31 mmol) was dissolved in 50 mL of dichloroethane and 50 mL of t-butyl alcohol, and 5-aminoindole (4.09 g, 31 mmol) were added. The reaction mixture was refluxed for 14 hours, cooled to room temperature, and concentrated in vacuo to afford 13.02 g of (6-bromo-thieno[3,2-d]pyrimidin-4-yl)-(1H-indol-5-yl)-amine. The crude material was used without further purification (83% purity). 1H NMR (400 MHz, DMSO) d 11.1 (s, 1H), 9.62 (s, 1H), 8.38 (s, 1H), 7.63 (s, 1H), 7.49 (s, 1H), 7.35 (m, 2H), 7.10 (d, 1H), 6.40 (s, 1H); LC-MS: 345, 347 (MH+); HPLC RT: 3.77 minutes.

Workup

  1. temperatureThe reaction mixture was refluxed for 14 hours
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2cf66ab01cb4f77b32d4357fdca74f0
Source dataset
uspto-grants-2002_12
Patent number
US06492383B1

Reaction notes

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