1,2-Dibromoethane → HCID 66691886, compound

HRID 1506570Notes

Reaction equation

HRID 1506570 reaction equation
[CH3:1][C:2]([CH3:15])=[CH:3][CH2:4][NH:5][C:6]1[N:14]=[CH:13][N:12]=[C:11]2[C:7]=1[NH:8][CH:9]=[N:10]2.[Br:16][CH2:17][CH2:18]Br.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CS(C)=O>[CH3:1][C:2]([CH3:15])=[CH:3][CH2:4][NH:5][C:6]1[N:14]=[CH:13][N:12]=[C:11]2[C:7]=1[N:8]=[CH:9][N:10]2[CH2:18][CH2:17][Br:16]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 921806-(3-Methyl-2-buten-1-ylamino)purine

Product 1

HCID 66691886HCID 66691886, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Mixture of 6-[(3-methylbut-2-en-1-yl)amino]purine (2 g, 9.8 mmol), 1,2-dibromoethane (12.94 g, 6 ml, 69 mmol) and K2CO3 (2.5 g, 24 mmol) was stirred in 50 ml DMSO for 12 h. Reaction mixture was poured onto drift ice and after ice dissolution 30 ml ethyl acetate was added. Ethyl acetate layer was purified by charcoal and SiO2 and then it was evaporated in vacuo. The pure product was recrystallised from methanol; yellow solid was obtained. Yield: 70%. 1H NMR (DMSO-d6): 1.75 (3H, s), 1.59 (3H, s), 4.12 (2H, t, J=5.76), 4.10 (2H, s (br)), 4.6 (2H, t, J=5.76), 5.3 (1H, t, J=6.57), 8.1 (1H, s (br)), 8.3 (1H, s).

Workup

  1. customReaction mixture
  2. additionwas poured onto drift ice
  3. additionwas added
  4. customEthyl acetate layer was purified by charcoal and SiO2
  5. customit was evaporated in vacuo
  6. customThe pure product was recrystallised from methanol
  7. customyellow solid was obtained

Sources & evidence

ORD record
ord-c36920d50f604a2ea54f252da4b05e36
Source dataset
uspto-grants-2015_12
Patent number
US09220269B2

Reaction notes

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