HCID 59299534, compound → HCID 59299559, compound

HRID 2386634Notes

Reaction equation

HRID 2386634 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11](CC=C)[C:10]([C:18]#[N:19])=[N:9][C:8]=2[N:7]([CH2:20][CH2:21][CH2:22][CH3:23])[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]>C1COCC1.CS(C)=O.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>[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([C:18]#[N:19])=[N:9][C:8]=2[N:7]([CH2:20][CH2:21][CH2:22][CH3:23])[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 59299534HCID 59299534, compound

Product 1

HCID 59299559HCID 59299559, compoundYield 24.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,3-dibutyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carbonitrile (140 mg, 0.43 mmol) in anhydrous THF (4 ml) and anhydrous DMSO (0.4 ml) was treated with Pd(PPh3)4 (74 mg, 0.064 mmol). The mixture was degassed under gentle vacuum, morpholine (371 uL) added, and left to stir at rt under nitrogen for 4 hours. The yellow solution was partitioned between 2M HCl(aq) and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated. The residue was taken up in MeOH and passed down and amino-propyl SPE (5 g), eluting with MeOH followed by 5%→50% AcOH/MeOH. The product eluted with a small impurity which was washed out, after concentrating, with cyclohexane to afford the title compound as an off-white solid (30 mg, 24%). NMR δH (400 MHz, d6-DMSO) 0.89 (app. td, 6H, J=7 and 3 Hz), 1.25-1.35 (m, 4H), 12.48-1.55 (m, 2H), 1.58-1.69 (m, 2H), 3.87 (t, 2H, J=7 Hz), 3.95 (t, 2H, J=7 Hz), NH not observed to δH 15; m/z 290.3 [MH+].

Workup

  1. customThe mixture was degassed under gentle vacuum, morpholine (371 uL)
  2. additionadded
  3. waitleft
  4. customThe yellow solution was partitioned between 2M HCl(aq) and EtOAc
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. washamino-propyl SPE (5 g), eluting with MeOH
  10. washThe product eluted with a small impurity which
  11. washwas washed out
  12. concentrationafter concentrating, with cyclohexane

Sources & evidence

ORD record
ord-0093f790909644e7853e3681490dd677
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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