1,1'-Carbonyldiimidazole → Kfm 19

HRID 1734178ノート

反応式

HRID 1734178 の反応式
[O:1]1[C:5]2([CH2:9][CH2:8][CH:7]([C:10](O)=O)[CH2:6]2)OCC1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][C:26]1[C:27](=[O:40])[N:28]([CH2:37][CH2:38][CH3:39])[C:29](=[O:36])[N:30]([CH2:33][CH2:34][CH3:35])[C:31]=1[NH2:32]>C(Cl)Cl>[CH2:37]([N:28]1[C:27](=[O:40])[C:26]2[NH:25][C:10]([CH:7]3[CH2:8][CH2:9][C:5](=[O:1])[CH2:6]3)=[N:32][C:31]=2[N:30]([CH2:33][CH2:34][CH3:35])[C:29]1=[O:36])[CH2:38][CH3:39]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 214672221,4-Dioxaspiro[4.4]nonane-7-carboxylic acid

生成物 1

HCID 131584Kfm 19収率 17.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2.4 g (0.014 mol) of 1,4-dioxaspiro[4,4]nonan-7-carboxylic acid are dissolved in 56 ml of methylene chloride and after the addition of 2.2 g (0.014 mol) of carbonyldiimidazole stirred for 1 hour at ambient temperature. Then 3.2 g (0.014 mol) of 5,6-diamino-1,3dipropyluracil are added and the mixture is stirred for a further 4 hours at ambient temperature. The solution is evaporated down in vacuo, the oily residue is mixed with 70 ml of water and 4.5 g of Ca(OH)2 and stirred for 1 hour at 70° C. 100 ml of 50% NaOH are added, the mixture is stirred for a further hour at 70° C. and for 16 hours at ambient temperature. Whilst being cooled with ice, the solution is adjusted to pH 6 with HCl and extracted with methylene chloride. After drying and evaporation in vacuo the combined organic phases yield a crystalline residue which is recrystallised from ethanol using activated charcoal. 0.8 g (16%) of white crystals are obtained, m.p. 147°-148° C.

後処理

  1. stirringthe mixture is stirred for a further 4 hours at ambient temperature
  2. customThe solution is evaporated down in vacuo
  3. additionthe oily residue is mixed with 70 ml of water and 4.5 g of Ca(OH)2
  4. stirringstirred for 1 hour at 70° C
  5. addition100 ml of 50% NaOH are added
  6. stirringthe mixture is stirred for a further hour at 70° C. and for 16 hours at ambient temperature
  7. temperatureWhilst being cooled with ice
  8. extractionextracted with methylene chloride
  9. customAfter drying
  10. customevaporation in vacuo the combined organic phases
  11. customyield a crystalline residue which
  12. customis recrystallised from ethanol using activated charcoal

出典と根拠

ORDレコード
ord-eb269ba8bec4400a83b316f5f71bd53e
出典データセット
uspto-grants-1996_07
特許番号
US05532368

反応ノート

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