Acetic Acid → 7-Benzyl-3-butylxanthine

HRID 2386647Notes

Reaction equation

HRID 2386647 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[NH:12][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH2:26][CH2:27][CH3:28].C(O)(=O)C>CN(C=O)C>[CH2:25]([N:12]1[C:11]2[N:10]=[CH:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]=2[C:15](=[O:17])[NH:14][C:13]1=[O:18])[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 125005077-Benzyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 39938667-Benzyl-3-butylxanthineYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-benzyl-3,7-dihydro-1H-purine-2,6-dione (17.14 g, 70.8 mmol) [Synthetic Communications, 20(16), 2459-2467, 1990] and potassium carbonate (11.43 g, 82.8 mmol) were suspended in DMF (400 mL) at 40° C. After stirring for thirty minutes, butyl iodide (8.76 mL, 77.0 mmol) was added, and the mixture was stirred at 40° C. overnight. 50% Aqueous acetic acid (60 mL) was added, and the solution was concentrated under reduced pressure. The residue was suspended in water (500 mL), and the products were extracted into chloroform. The organics were collected, concentrated, and product was isolated using flash chromatography eluting with 1% methanol in dichloromethane to provide the product (9.49 g, 45%); 1H NMR (400 MHz; CDCl3) δ: 0.95 (3H, t), 1.34-1.41 (2H, m), 1.70-1.78 (2H, m), 4.05 (2H, t), 5.46 (2H, s), 7.31-7.40 (5H, m), 7.56 (1H, s), 8.21 (1H, br.s); m/z 299 [MH+].

Workup

  1. stirringthe mixture was stirred at 40° C. overnight
  2. concentrationthe solution was concentrated under reduced pressure
  3. extractionthe products were extracted into chloroform
  4. customThe organics were collected
  5. concentrationconcentrated
  6. customproduct was isolated
  7. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-764959fe6d3443aa9a5364c5190f6423
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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