Sodium hydride → 3-(2-Furylmethyl)-7-pivaloyloxymethyl-8-methylxanthine

HRID 1421238Notes

Reaction equation

HRID 1421238 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15]2[N:14]=[C:13]([CH3:16])[NH:12][C:11]=2[C:10](=[O:17])[NH:9][C:8]1=[O:18].[H-].[Na+].[C:21]([O:27][CH2:28]Cl)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>CS(C)=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15]2[N:14]=[C:13]([CH3:16])[N:12]([CH2:28][O:27][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:11]=2[C:10](=[O:17])[NH:9][C:8]1=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 187805573-(2-Furylmethyl)-8-methylxanthine

Product 1

HCID 187805583-(2-Furylmethyl)-7-pivaloyloxymethyl-8-methylxanthineYield 69%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring solution of 3-(2-furylmethyl)-8-methylxanthine (1.35 g, 5.48 mmol) in dimethyl sulfoxide (20 ml) was added sodium hydride (132 mg, 5.48 mmol) in one portion. After 30 minutes, chloromethyl pivalate (0.83 ml, 5.76 mmol) was added neat. The reaction was allowed to stir at ambient temperature for 24 h. The reaction was quenched by slow addition of water (75 ml). After stirring for 3 hours, the solid was filtered and rinsed with water (4×50 ml) and ethanol (50 ml). The product was recrystallized from ethanol/ethyl acetate/hexane to give 3-(2-Furylmethyl)-7-pivaloyloxymethyl-8-methylxanthine (1.36 g, 69%) as an off-white solid.

Workup

  1. customThe reaction was quenched by slow addition of water (75 ml)
  2. stirringAfter stirring for 3 hours
  3. filtrationthe solid was filtered
  4. washrinsed with water (4×50 ml) and ethanol (50 ml)
  5. customThe product was recrystallized from ethanol/ethyl acetate/hexane

Sources & evidence

ORD record
ord-801770e453f94b07b454998fc99e4d03
Source dataset
uspto-grants-2000_06
Patent number
US06075029

Reaction notes

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