Adenine → 8-Bromoadenine

HRID 1295473Notes

Reaction equation

HRID 1295473 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[Br:11]Br.N>C(Cl)(Cl)Cl>[Br:11][C:6]1[NH:7][C:8]2[C:4](=[N:3][CH:2]=[N:1][C:9]=2[NH2:10])[N:5]=1

Participants

5

Reactant 3

HCID 190AdenineHCID 222AmmoniaHCID 24408Bromine

Product 1

HCID 814578-BromoadenineYield 60.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Adenine (47 g, 0.35 mole) was suspended in 200 ml of CHCl3 before adding bromine (180 ml, 3.5 mole) in one portion. The suspension was left stirring at room temperature for 72 hours in a closed system that was vented by a 20 G needle. The reaction was worked up by adding shaved ice into the suspension before slowly neutralizing with aqueous ammonia to pH 8-9, followed by precipitation of the desired product with acetic acid. The crude product was dried under reduced pressure for 2 days to give 8-Bromoadenine as a light brown powder (45 g, 60% yield). 1H NMR (DMSO-d6) δ 8.12 (s, 1H), 7.22 (s, 2H). Rf(75% EtOAc/Hex)=0.4.

Workup

  1. waitThe suspension was left
  2. additionby adding
  3. customfollowed by precipitation of the desired product with acetic acid
  4. dry with materialThe crude product was dried under reduced pressure for 2 days

Sources & evidence

ORD record
ord-faa4185b059c4f1caf1b82807622e3d5
Source dataset
uspto-grants-2007_07
Patent number
US07241890B2

Reaction notes

Loading…