Ethyl cyanoacetate → 6-Amino-1-propyluracil

HRID 1507616

反応式

HRID 1507616 の反応式
[O-:1][CH2:2][CH3:3].[Na+].[C:5](CC(OCC)=O)#[N:6].[CH2:13]([NH:16][C:17]([NH2:19])=[O:18])[CH2:14][CH3:15]>C(O)C>[NH2:6][C:5]1[N:16]([CH2:13][CH2:14][CH3:15])[C:17](=[O:18])[NH:19][C:2](=[O:1])[CH:3]=1

参加物

5

反応物 3

HCID 7764Ethyl cyanoacetateHCID 12303PropylureaHCID 2723922Sodium ethoxide

生成物 1

HCID 1045626-Amino-1-propyluracil収率 96%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Sodium ethoxide (19.99 g, 293.72 mmol, 2 eq) was dissolved in anhydrous ethanol (210 ml) at 50° C. To the solution was added ethyl 2-cyanoacetate (15.67 ml, 146.86 mmol, 1 eq) then 1-propylurea (15 g, 146.86 mmol, 1 eq), and the mixture was stirred at reflux for 24 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in water (70 ml). The pH of the solution was adjusted to ˜7 by using concentrated HCl. The light yellow solid formed was collected by filtration, washed with water, and dried under vacuum to afford 23.82 g of the desired product (96% yield): The desired isomer was determined via 2D-NMR; 1H NMR (400 MHz, DMSO-d6) δ 10.3 (1H), 6.79 (2H), 4.52 (1H), 3.68-3.70 (2H), 1.50 (2H), 0.85 (3H); m/z (ES+) 170.18

後処理

  1. temperatureat reflux for 24 hours
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water (70 ml)
  4. customThe light yellow solid formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-6455bbbd7eeb4c738ffce38197e6e79f
出典データセット
uspto-grants-2015_12
特許番号
US09221821B2

関連ノート

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