Cesium carbonate → HCID 59395626, compound

HRID 1097675Notes

Reaction equation

HRID 1097675 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10]([CH2:15][CH:16]=[CH2:17])[C:9]=2[C:8](=[O:18])[NH:7][C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:27]([CH2:30][CH3:31])[C:28]#[N:29]>CC#N>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10]([CH2:15][CH:16]=[CH2:17])[C:9]=2[C:8](=[O:18])[N:7]([CH2:31][CH2:30][CH2:27][C:28]#[N:29])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 131794392-BromobutanenitrileHCID 592995823-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 59395626HCID 59395626, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

3-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (2.0 g, 0.0072 mol) in dry MeCN (20 ml) was added Cs2CO3 (4.68 g, 0.0144 mol) followed by bromobutyronitrile (1.38 g, 0.0094 mol). The mixture was heated at 80° C. for 18 h and then allowed to cool. The reaction mixture was evaporated and the crude product partitioned between EtOAc and HCl (2N). The organic phase was separated and washed with brine, dried (MgSO4) and evaporated to give the crude product. This was purified by silica SPE (50 g), eluting with cyclohexane:ethylacetate (2:1 to 1:1) to afford the title compound as a clear oil (2.1 g, 85%).

Workup

  1. temperatureto cool
  2. customThe reaction mixture was evaporated
  3. customthe crude product partitioned between EtOAc and HCl (2N)
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give the crude product
  9. customThis was purified by silica SPE (50 g)
  10. washeluting with cyclohexane:ethylacetate (2:1 to 1:1)

Sources & evidence

ORD record
ord-2eb97e70843c40abb08dd945d22cc233
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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