1,1'-Carbonyldiimidazole → Kfm 19

HRID 1939232Notes

Reaction equation

HRID 1939232 reaction equation
[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]

Participants

5

Reactant 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

Product 1

HCID 131584Kfm 19Yield 17.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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-1,3-dipropyluracil 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.

Workup

  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

Sources & evidence

ORD record
ord-e9f5b298556d44c1912690f3b8a6f392
Source dataset
uspto-grants-1997_12
Patent number
US05696124

Reaction notes

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