Water → 6-Amino-8-(4-isobutoxy-3-nitrophenyl)purine

HRID 851862Notes

Reaction equation

HRID 851862 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=O)=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16])[CH:2]([CH3:4])[CH3:3].S(O)(O)(=O)=O.[NH2:23][C:24]1[C:29]([NH2:30])=[C:28]([NH2:31])[N:27]=[CH:26][N:25]=1.O>O1CCOCC1.[OH-].[Na+]>[NH2:31][C:28]1[N:27]=[CH:26][N:25]=[C:24]2[C:29]=1[NH:30][C:10]([C:9]1[CH:13]=[CH:14][C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[C:7]([N+:15]([O-:17])=[O:16])[CH:8]=1)=[N:23]2

Participants

6

Reactant 3

HCID 962WaterHCID 1115444,5,6-Pyrimidinetriamine, sulfate (1:1)HCID 23023854HCID 23023854, compound

Product 1

HCID 98188136-Amino-8-(4-isobutoxy-3-nitrophenyl)purineYield 21%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

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.

Workup

  1. temperatureunder cooling with ice
  2. filtrationThe precipitated solid product was collected by filtration
  3. customdried in air

Sources & evidence

ORD record
ord-fd2f0aaa3dcb4da1b870f213ae7135ac
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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