Allylamine → 2,4,7-Triallylaminothieno[3,2-d]pyrimidine

HRID 1250694Notes

Reaction equation

HRID 1250694 reaction equation
[CH2:1]([NH:4][C:5]1[N:6]=[C:7]([NH:15][CH2:16][CH:17]=[CH2:18])[C:8]2[S:13][CH:12]=[C:11](Br)[C:9]=2[N:10]=1)[CH:2]=[CH2:3].[CH2:19]([NH2:22])[CH:20]=[CH2:21].C(=O)([O-])[O-].[K+].[K+]>[Cu]>[CH2:1]([NH:4][C:5]1[N:6]=[C:7]([NH:15][CH2:16][CH:17]=[CH2:18])[C:8]2[S:13][CH:12]=[C:11]([NH:22][CH2:19][CH:20]=[CH2:21])[C:9]=2[N:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 11430Potassium CarbonateHCID 183264202,4-Diallylamino-7-bromothieno[3,2-d]pyrimidine

Product 1

HCID 183264232,4,7-Triallylaminothieno[3,2-d]pyrimidineYield 72.9%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

120 mg (0.37 mmol) of 2,4-diallylamino-7-bromothieno[3,2-d]pyrimidine, 337 mg (5.9 mmol) of allylamine, 56 mg (0.41 mmol) of potassium carbonate and 1 mg of copper were heated in a sealed tube at 180° C. for 5 hours. After completion of the reaction, the reaction mixture was allowed to resume room temperature, followed by distilling off excess allylamine under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/8) to give 81 mg (yield: 72.9%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customto resume room temperature
  3. distillationby distilling off excess allylamine under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/8)

Sources & evidence

ORD record
ord-94761747e999438f8e52170d0b8bc2f7
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

Loading…