Acetic Acid → 7-Benzyl-3-butylxanthine

HRID 2234962

반응식

HRID 2234962 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 39938667-Benzyl-3-butylxanthine수율 45%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-c60e62b786e647abb187e6629f772184
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713982B2

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