1-Bromo-2-Chloroethane → HCID 68298457, compound

HRID 1506571Notes

Reaction equation

HRID 1506571 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[CH2:17][CH2:18][Cl:19].C([O-])([O-])=O.[K+].[K+]>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[CH2:17][CH2:18][Cl:19]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 921806-(3-Methyl-2-buten-1-ylamino)purine

Product 1

HCID 68298457HCID 68298457, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-[(3-methylbut-2-en-1-yl)amino]purine (2 g, 9.8 mmol), 1-bromo-2-chloroethane (1.4 g, 9.8 mmol) and K2CO3 (3 g, 29 mmol) were stirred in 50 ml DMSO for 12 h. The reaction mixture was poured onto ice (200 ml) and extracted in ethylacetate (50 ml). The solid residue was recrystallized from hexane to obtain white crystals. Yield: 60%. 1H NMR (DMSO-d6): 1.66 (3H, s), 1.70 (3H, s), 4.06 (2H, t, J=5.76), 4.10 (2H, s (br), H12), 4.50 (2H, t, J=5.76), 5.31 (1H, t, J=6.57), 7.767 (1H, s (br)), 8.15 (1H, s), 8.20 (1H, s).

Workup

  1. additionThe reaction mixture was poured onto ice (200 ml)
  2. extractionextracted in ethylacetate (50 ml)
  3. customThe solid residue was recrystallized from hexane
  4. customto obtain white crystals

Sources & evidence

ORD record
ord-455c82da8a5345dd8e2b3f46f523009f
Source dataset
uspto-grants-2015_12
Patent number
US09220269B2

Reaction notes

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