Water → HCID 17954008, compound

HRID 1432380Notes

Reaction equation

HRID 1432380 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[N:3]=1.[H-].[Na+].Br[CH:24]([CH3:26])[CH3:25].O>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:24]([CH3:26])[CH3:25])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 178526635HCID 178526635, compound

Product 1

HCID 17954008HCID 17954008, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Chloro-9H-purin-6-yl)-(3-nitro-phenyl)-amine (872 mg, 3 mmol) was dissolved in dry DMF (10 mL). NaH (122 mg, 5.1 mmol) was added in portions and the resulting mixture was stirred for 1 h. 2-Bromopropane (480 mg, 3.9 mmol) was then added and the reaction was stirred overnight at 80° C. under N2. After cooling, H2O (50 mL) was added slowly with stirring and cooling. After 1 h, precipitated product was filtered, washed with more cold H2O, and dried in vacuo to afford the title compound as a lemon-yellow powder (905 mg, 90.7%). TLC (95:5 CH2Cl2/MeOH): RF=0.46.

Workup

  1. stirringthe reaction was stirred overnight at 80° C. under N2
  2. temperatureAfter cooling
  3. stirringwith stirring
  4. temperaturecooling
  5. waitAfter 1 h
  6. customprecipitated product
  7. filtrationwas filtered
  8. washwashed with more cold H2O
  9. customdried in vacuo

Sources & evidence

ORD record
ord-90fe7b29a3964520abbc2c4ea0b9d2aa
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Reaction notes

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