Ammonium Chloride → HCID 59835091, compound

HRID 271274Notes

Reaction equation

HRID 271274 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:14]=[C:13]([NH2:15])[N:12]=[C:11]2[C:7]=1[N:8]=[CH:9][N:10]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[NH4+].[Cl-]>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:14]=[C:13]([NH2:15])[N:12]=[C:11]2[C:7]=1[N:8]=[CH:9][N:10]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium Fluoride2×HCID 9966890HCID 9966890, compound

Product 1

HCID 59835091HCID 59835091, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

An ice-cold solution of 6-(2-furyl)-9-(3-methoxybenzyl)-9H-purine-2-amine (160 mg, 0.5 mmol) in DCM (3 mL) was treated with BBr3 (1 mL, 1-M in DCM, 1 mmol), stirred at 0° C. for 3 h, treated with more BBr3 (2 ml, 1-M in DCM, 2 mmol), stirred for 16 h, treated with NH4Cl solution, extracted with EtOAc, dried (MgSO4), concentrated in vacuo, triturated with ether and filtered. The resulting solid was suspended in aqueous sodium bicarbonate, extracted with ether, the aqueous phase was acidified to pH 7 and the resulting solid filtered, suspended in methanol, treated with HCl in dioxane (4-M, 2 mL), diluted with ether and filtered to give the title compound (82 mg, 48%) as a yellow solid.

Workup

  1. stirringstirred for 16 h
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customtriturated with ether
  6. filtrationfiltered
  7. extractionextracted with ether
  8. filtrationthe resulting solid filtered
  9. additiontreated with HCl in dioxane (4-M, 2 mL)
  10. additiondiluted with ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-e4897d0fb773404e8c4ac77bc9913de7
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

Loading…