Sodium hydride → HCID 23516881, compound

HRID 1814951Notes

Reaction equation

HRID 1814951 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:15])[NH:5][C:4](=[O:16])[C:3]=1[NH:17][CH3:18].[H-].[Na+].[C:21]([O:24][C@H:25]([CH3:31])[CH2:26][CH2:27][CH2:28][CH2:29]Cl)(=[O:23])[CH3:22]>CS(C)=O>[C:21]([O:24][C@H:25]([CH3:31])[CH2:26][CH2:27][CH2:28][CH2:29][N:5]1[C:4](=[O:16])[C:3]([NH:17][CH3:18])=[C:2]([NH2:1])[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]1=[O:15])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 7262256-AMINO-1-BENZYL-5-METHYLAMINOURACILHCID 110194345-(R)-Acetoxy-1-chlorohexane

Product 1

HCID 23516881HCID 23516881, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

6-Amino-1-benzyl-5-methylaminouracil (11 g, 43 mmol) was added to a suspension of sodium hydride (1.032 mg, 43 mmol) in anhydrous dimethylsulfoxide (75 ml). After stirring for 30 minutes, (R)-5-acetoxy-1-chlorohexane (7.675 g, 43 mmol) was added. The mixture was heated at 70-80° C. for 12 hours. After cooling to room temperature, the reaction was quenched by the addition of water (150 ml) and extracted with ethyl acetate (3x 125 ml). The combined extracts were washed with water (2x 50 ml), with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to provide (R)-3-(5-acetoxyhexyl)-6-amino-1-benzyl-5-methylaminouracil (7.89 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was quenched by the addition of water (150 ml)
  3. extractionextracted with ethyl acetate (3x 125 ml)
  4. washThe combined extracts were washed with water (2x 50 ml), with saturated aqueous sodium chloride solution (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-52ef98fa37b4440e90c7e525af8bf29a
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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