Potassium Carbonate → HCID 86684662, compound

HRID 926430Notes

Reaction equation

HRID 926430 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[CH:9].[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[N:23]=[C:22]([NH2:24])[N:21]=[C:20]2[C:16]=1[NH:17][CH:18]=[N:19]2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[N:23]=[C:22]([NH2:24])[N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[CH:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111061218-bromo-1-octyneHCID 178143546-(Thiophen-2-yl)-7H-purin-2-amine

Product 1

HCID 86684662HCID 86684662, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Bromo-1-octyne (2.0 g, 10.6 mmol) prepared in step 1) was added to a dehydrated dimethylformamide (25 mL) solution containing 6-(thien-2-yl)-2-amino purine (1.2 g, 5.5 mmol) and potassium carbonate (2.3 g, 16.5 mmol), followed by stirring at room temperature for 15 hours. The reaction solution was concentrated and was separated between ethyl acetate and water. The organic layer was washed with saturated brine, was dried over anhydrous sodium sulfate, and was purified by medium-pressure preparative column chromatography to yield 6-(thien-2-yl)-9-(7-octynyl)-2-amino purine (1.6 g, 4.9 mmol, 87%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customwas separated between ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customwas purified by medium-pressure preparative column chromatography

Sources & evidence

ORD record
ord-90e6db68316d4dfa927c48f9c825242b
Source dataset
uspto-grants-2016_03
Patent number
US09285319B2

Reaction notes

Loading…