8-ethyl-7-(4-heptyl)-3-(4-methoxybenzyl)-1-methyl-3,7-dihydro-1H-purine-2,6-dione → HCID 11150504, compound

HRID 11284Notes

Reaction equation

HRID 11284 reaction equation
[CH2:1]([C:3]1[N:11]([CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[C:10]2[C:9](=[O:19])[N:8]([CH3:20])[C:7](=[O:21])[N:6](CC3C=CC(OC)=CC=3)[C:5]=2[N:4]=1)[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([C:3]1[N:11]([CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[C:10]2[C:9](=[O:19])[N:8]([CH3:20])[C:7](=[O:21])[NH:6][C:5]=2[N:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 695925988-ethyl-7-(4-heptyl)-3-(4-methoxybenzyl)-1-methyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 11150504HCID 11150504, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 8-ethyl-7-(4-heptyl)-3-(4-methoxybenzyl)-1-methyl-3,7-dihydro-1H-purine-2,6-dione in trifluoroacetic acid was heated at 100° C. in a sealed tube for 8 h. The mixture was cooled to r.t. and concentrated. The residue was transferred into a separatory funnel containing saturated aqueous NaHCO3 (20 mL) and the aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (5% methanol in CH2Cl2) to afford a colorless solid (645 mg, 91% yield): mp 152.5–153° C.; 1H NMR (300 MHz, CDCl3) δ 12.0 (s, 1H), 4.20–4.10 (m, 1H), 3.41 (s, 3H), 2.94 (q, J=7.3 Hz, 2H), 2.33–2.19 (m, 2H), 1.94–1.83 (m, 2H), 1.42 (t, J=7.4 Hz, 3H), 1.26–1.06 (m, 4H), 0.90 (t, J=7.3 Hz, 6H); LRMS (APCI) m/e 293.1 [(M+H)+, calcd for C15H25N4O2 293.2].

Workup

  1. concentrationconcentrated
  2. customThe residue was transferred into a separatory funnel
  3. additioncontaining saturated aqueous NaHCO3 (20 mL)
  4. extractionthe aqueous layer was extracted with EtOAc (3×30 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-a85b175f5e694e069515cd19d8b62070
Source dataset
uspto-grants-2006_08
Patent number
US07098217B2

Reaction notes

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