Reaction #939044

ord-fd2f0aaa3dcb4da1b870f213ae7135ac

Reaction equation

CC(C)COc1ccc(C(=O)Cl)cc1[N+](=O)[O-]
4-isobutoxy-3-nitrobenzoyl chloride
Nc1ncnc(N)c1N.O=S(=O)(O)O
4,5,6-triaminopyrimidine sulfate
O
Water
→
CC(C)COc1ccc(-c2nc3ncnc(N)c3[nH]2)cc1[N+](=O)[O-]
desired compound
Yield 21.0%
CC(C)COc1ccc(-c2nc3ncnc(N)c3[nH]2)cc1[N+](=O)[O-]
6-Amino-8-(4-isobutoxy-3-nitrophenyl)purine
Yield 21.0%

Reactants

CC(C)COc1ccc(C(=O)Cl)cc1[N+](=O)[O-]
4-isobutoxy-3-nitrobenzoyl chloride
Nc1ncnc(N)c1N.O=S(=O)(O)O
4,5,6-triaminopyrimidine sulfate
O
Water

Reagents

None

Solvents

C1COCCO1
1,4-dioxane
[Na+].[OH-]
sodium hydroxide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureunder cooling with ice
  2. 2
    FiltrationThe precipitated solid product was collected by filtration
  3. 3
    Otherdried in air

Procedure

A solution of 4-isobutoxy-3-nitrobenzoyl chloride (538 mg, 2.09 mmol) in 1,4-dioxane (2 mL) was dropwise added to a suspension of 4,5,6-triaminopyrimidine sulfate (466 mg, 2.09 mmol) in aqueous 1M sodium hydroxide (4.18 30 mL) under cooling with ice. The resulting mixture was stirred for 4 hours at the same temperature. Water (12 mL) was added to the reaction mixture. The precipitated solid product was collected by filtration, dried in air, and subjected to silica gel column chromatography. The elute using chloroform/methanol (10/1) gave 144 mg (yield 20%) of the desired compound in the form of a yellow powdery product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07253154B2uspto-grants-2007_08