Dimethyl Sulfoxide → HCID 59299535, compound

HRID 2386623Notes

Reaction equation

HRID 2386623 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8](CC=C)[C:7]([C:15]#[N:16])=[N:6][C:5]=2[N:4]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]1=[O:22].N1CCOCC1.CS(C)=O>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>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[NH:8][C:7]([C:15]#[N:16])=[N:6][C:5]=2[N:4]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]1=[O:22]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 592995381-Methyl-2,6-dioxo-3-pentyl-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile

Product 1

HCID 59299535HCID 59299535, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-Methyl-2,6-dioxo-3-pentyl-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile (0.17 g, 0.56 mmol) and morpholine (0.6 ml, 6.7 mmol) were dissolved in THF (5 ml) containing DMSO (0.5 ml). The flask containing the solution was placed under vacuum and the air replaced with nitrogen (×3). Tetrakis(triphenylphosphine)palladium (0) (0.13 g, 0.11 mmol) was added and the solution stirred for 2.5 h. The solution was separated between ethyl acetate (20 ml) and 2N hydrochloric acid (10 ml) and the organics isolated and washed with brine (3×10 ml). The organics were then washed with 2N sodium hydroxide solution (2×10 ml) and the aqueous acidified with 2N hydrochloric acid and extracted with ethyl acetate (2×10 ml). The organics were isolated, dried (MgSO4) and concentrated to yield the title compound (0.026 g, 18%). NMR; δH (400 MHz, CDCl3) 0.92 (t, 3H, J=7 Hz), 1.32-1.43 (m, 4H), 1.79 (m, 2H), 3.54 (s, 3H), 4.15 (t, 2H, J=7.5 Hz), 14.35 (br. s, 1H); m/z 262 [MH+]

Workup

  1. additionThe flask containing the solution
  2. customThe solution was separated between ethyl acetate (20 ml) and 2N hydrochloric acid (10 ml)
  3. customthe organics isolated
  4. washwashed with brine (3×10 ml)
  5. washThe organics were then washed with 2N sodium hydroxide solution (2×10 ml)
  6. extractionextracted with ethyl acetate (2×10 ml)
  7. customThe organics were isolated
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-66c415974ef241d3a4f52cb6c44807c5
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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