1-Bromo-2-methylpropane → 2-Chloro-9-isobutyl-6-morpholin-4-yl-9H-purine

HRID 421295Notes

Reaction equation

HRID 421295 reaction equation
[CH2:1](Br)[CH:2]([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][NH:19]2)=[C:15]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:14]=1>CN(C)C=O>[Cl:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:1][CH:2]([CH3:4])[CH3:3])=[C:15]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[N:14]=1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 32746034-(2-chloro-9H-purin-6-yl)morpholine

Product 1

HCID 580152192-Chloro-9-isobutyl-6-morpholin-4-yl-9H-purineYield 103.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N,N-Dimethylformamide (60 ml), isobutyl bromide (2 ml, 18 mmol), and potassium carbonate (3 g) were added to 2-chloro-6-morpholin-4-yl-9H-purine (5 g, 17 mmol) and the resulting mixture was stirred at 80° C. for 5 hours. The reaction mixture was cooled and partitioned with ethyl acetate and water and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (5.2 g, 100%) as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned with ethyl acetate and water
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0dd0b59b1f2849539f64b92642666dc4
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

Loading…