Bromine → HCID 23079447, compound

HRID 1684971Notes

Reaction equation

HRID 1684971 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:13]=2)=[C:4]([NH2:23])[N:3]=1.C([O-])(=O)C.[Na+].[Br:29]Br>C(Cl)(Cl)Cl>[Br:29][C:7]1[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:13]=2)[C:9]2[C:5]([N:6]=1)=[C:4]([NH2:23])[N:3]=[C:2]([Cl:1])[N:10]=2

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 230794762-Chloro-9-(3-methoxycarbonylmethylbenzyl)adenine

Product 1

HCID 23079447HCID 23079447, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

After 2-chloro-9-(3-methoxycarbonylmethylbenzyl)adenine obtained by Reference example 38 (2.00 g, 6.03 mmol) and sodium acetate (2.95 g, 36.0 mmol) were dissolved in chloroform (100 ml), bromine (4.79 g, 30.0 mmol) was added thereto and the mixture was stirred at room temperature for 5 hours. After removing the solvent, the residue was poured into water and extracted with chloroform. The organic layer was washed with saturated sodium hydrogencarbonate, saturated sodium hydrogensulfite and saturated brine in that order, dried over anhydrous magnesium sulfate and concentrated to give the captioned compound (1.78 g, 4.34 mmol, yield: 72%) as a brown solid.

Workup

  1. customAfter removing the solvent
  2. additionthe residue was poured into water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated sodium hydrogencarbonate, saturated sodium hydrogensulfite and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-50deafc8836e47989691399fe771f4bf
Source dataset
uspto-grants-2012_04
Patent number
US08148371B2

Reaction notes

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