Dimethyl Sulfoxide → 8-Chloro-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1943795Notes

Reaction equation

HRID 1943795 reaction equation
[Cl:1][C:2]1[N:10](CC=C)[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.CS(C)=O.N1CCOCC1>C1COCC1.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[NH:10][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

Participants

7

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 462157998-Chloro-3-pentyl-3,7-dihydro-1H-purine-2,6-dioneYield 33%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A flask containing tetrakis(triphenylphosphine)-palladium (0) (56 mg, 0.049 mmol) was flushed with nitrogen, before a solution of 8-chloro-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (96 mg, 0.323 mmol) in anhydrous THF (1.5 ml) was added, followed by DMSO (0.1 ml) and morpholine (0.28 ml, 0.049 mmol). The resulting mixture was stirred at room temperature under nitrogen for 72 hours. The reaction mixture was dissolved in EtOAc (25 ml) and washed with 2M HCl aq. (25 ml). The organic extract was dried (MgSO4) filtered and evaporated under reduced pressure. Purification by amino propyl SPE (2 g) loading and washing with methanol and then eluting the product with 5% acetic acid in methanol. Evaporation of fractions containing product afforded the title compound as a white solid (27 mg, 33%). NMR; δH (400 MHz, d6-DMSO) 0.85 (t, 3H, J=7 Hz), 1.20-1.34 (m, 4H), 1.57-1.67 (m, 2H), 3.84 (t, 2H, J=7 Hz), 11.19 (s, 1H), 14.38 (br. s, 1H); m/z 257.2[MH+].

Workup

  1. additionwas added
  2. washwashed with 2M HCl aq. (25 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification by amino propyl SPE (2 g) loading
  8. washwashing with methanol
  9. washeluting the product with 5% acetic acid in methanol
  10. customEvaporation of fractions
  11. additioncontaining product

Sources & evidence

ORD record
ord-45cd9eaf5e6e40bd9506daaf70fad95a
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

Loading…