Methyl iodide → HCID 59299536, compound

HRID 2386643Notes

Reaction equation

HRID 2386643 reaction equation
[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1.[C:21](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[N:7]([CH3:21])[C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 59299536HCID 59299536, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-chloro-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (3.9 g, 13.3 mmol) in DMF (35 ml) was added cesium carbonate and the mixture stirred for 10 min whereupon iodomethane (0.91 ml, 14.6 mmol) was added and the mixture stirred for 18 h. The reaction was partitioned between ethyl acetate and 2N HCl solution and the organics isolated, dried (MgSO4) and concentrated. Chromatography on silica SPE eluting with cyclohexane/ethyl acetate (5%-20%) provided the product as an oil, 2.78 g, 68%. m/z 311 [MH+].

Workup

  1. additionwas added
  2. customThe reaction was partitioned between ethyl acetate and 2N HCl solution
  3. dry with materialthe organics isolated, dried (MgSO4)
  4. concentrationconcentrated
  5. washChromatography on silica SPE eluting with cyclohexane/ethyl acetate (5%-20%)

Sources & evidence

ORD record
ord-0799b415013f4042b8632f09988a35b8
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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