Tetrahydrofuran → HCID 67078499, compound

HRID 480102Notes

Reaction equation

HRID 480102 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10](C3CCCCO3)[CH:9]=[N:8][C:7]=2[N:6]([CH2:20][CH2:21][CH3:22])[C:5]1=[O:23])[CH2:2][CH3:3].[Li]CCCC.O[CH2:30][C:31]1([CH2:38][OH:39])[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1.C1C[O:43][CH2:42][CH2:41]1>>[O:23]=[C:5]1[N:6]([CH2:20][CH2:21][CH3:22])[C:7]2[N:8]=[C:9]([C:34]34[CH2:33][CH2:32][C:31]([CH2:38][O:39][C:42](=[O:43])[CH3:41])([CH2:36][CH2:35]3)[CH2:30][O:37]4)[NH:10][C:11]=2[C:12](=[O:13])[N:4]1[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 11427191HCID 11427191, compoundHCID 670787344,4-Bis(hydroxymethyl)cyclohexanoneHCID 178418339Butyllithium

Product 1

HCID 67078499HCID 67078499, compound

Procedure

1,3-Dipropyl-7-(tetrahydro-pyran-2-yl)-3,7-dihydro-purine-2,6-dione (5.30 g, 16.5 mmol) was dissolved in anhydrous THF (250 ml) and cooled to −78° C. nBuLi (2.5 M in hexanes, 6.60 ml, 1 eq) was added, followed by the ditosylate derivative of 4,4-bis-hydroxymethyl-cyclohexanone (7.7 g, 1 eq) and the reaction mixture was slowly warmed to RT and stirred at RT overnight. The next day, the reaction was quenched with sat'd. aq. NH4Cl. The reaction was diluted with water and extracted with EtOAc. The organic layer was dried and concentrated under reduced pressure. Purification by chromatography (2:1 hex/EtOAc) afforded 10.4 g of the ditoylate xanthine derivative.

Workup

  1. additionwas added
  2. customThe next day, the reaction was quenched with sat'd
  3. additionThe reaction was diluted with water
  4. extractionextracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography (2:1 hex/EtOAc)

Sources & evidence

ORD record
ord-a55fb8e0ef0d46788b5111a570146e14
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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