Dimethyl Sulfoxide → HCID 59299568, compound

HRID 2386644Notes

Reaction equation

HRID 2386644 reaction equation
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:4]=2[N:3]=1.CS(C)=O.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 59299536HCID 59299536, compound

Product 1

HCID 59299568HCID 59299568, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (1.0, 0.90 mmol) was placed in a flask which was evacuated and then filled with nitrogen (×3). A solution of 8-chloro-1-methyl-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (2.78 g, 8.96 mmol) in 50 ml of THF was added and the flask evacuated once more and nitrogen introduced. DMSO (4.5 ml) and morpholine (7.8 ml, 89.6 mmol) was added and the solution stirred for 5 h. The solution was partitioned between ethyl acetate and 2N HCl solution and the organic fraction washed with brine, dried (MgSO4) and concentrated. The crude was purified with an aminopropyl SPE eluting with first methanol then methanol containing 0-15% acetic acid to provide the title compound as a white solid, 1.12 g, 46%. NMR δH (400 MHz, d6-DMSO) 0.86 (t, 3H, J=7 Hz), 1.21-1.35 (m, 4H), 1.59-1.68 (m, 2H), 3.22 (s, 3H), 3.91 (t, 2H, J=7.5 Hz), NH not observed; m/z 271 [MH+].

Workup

  1. customwhich was evacuated
  2. additionfilled with nitrogen (×3)
  3. customthe flask evacuated once more
  4. additionnitrogen introduced
  5. customThe solution was partitioned between ethyl acetate and 2N HCl solution
  6. washthe organic fraction washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude was purified with an aminopropyl SPE
  10. washeluting with first methanol

Sources & evidence

ORD record
ord-8d6eee95b9094560b0dd4ed8d863fd2e
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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