Dimethylformamide → 8-Bromo-9-butyl-9H-purin-6-amine

HRID 1295474Notes

Reaction equation

HRID 1295474 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:4](=[N:5][CH:6]=[N:7][CH:8]=2)[N:3]=1.Br[CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+].C[N:23](C=O)C>>[Br:1][C:2]1[N:3]([CH2:12][CH2:13][CH2:14][CH3:15])[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:23])[N:7]=[CH:6][N:5]=2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 10796Cesium carbonateHCID 218830508-Bromo-7H-purine

Product 1

HCID 116087198-Bromo-9-butyl-9H-purin-6-amineYield 33%

Procedure

8-Bromopurine (2.2 g, 10 mmole) was dissolved in 50 ml of DMF before adding 1-bromo-butane (2.2 ml, 20 mmol) and cesium carbonate (6.7 g, 20 mmol) into the solution. The reaction mixture was left stirring at room temperature for 16 hours before quenching with water and extracting with EtOAc. The organic layer was w ashed with water and dried with MgSO4 before removing solvent under reduced pressure. A white powder (0.9 g, 33%) of 8-Bromo-9-butyl-9H-purin-6-ylamine was isolated using silica gel column chromatography (50% EtOAc/Hexanes). 1H NMR (CDCl3) δ 8.32, (s, 1H), 5.81 (s, 2H), 4.20 (t, 2H), 1.82 (m, 2H), 1.40 (m, 2H), 0.96 (t, 3H). Rf (75% EtOAc/Hex)=0.6.

Workup

  1. waitThe reaction mixture was left
  2. custombefore quenching with water
  3. extractionextracting with EtOAc
  4. dry with materialdried with MgSO4
  5. custombefore removing solvent under reduced pressure

Sources & evidence

ORD record
ord-dcc8d7e45348493a803da76577abbfe3
Source dataset
uspto-grants-2007_07
Patent number
US07241890B2

Reaction notes

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