1,1'-Carbonyldiimidazole → HCID 14795477, compound

HRID 1734177Notes

Reaction equation

HRID 1734177 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7](O)=O)[CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:22][C:23]1[C:24](=[O:37])[N:25]([CH2:34][CH2:35][CH3:36])[C:26](=[O:33])[N:27]([CH2:30][CH2:31][CH3:32])[C:28]=1[NH2:29]>C(Cl)Cl>[CH2:34]([N:25]1[C:24](=[O:37])[C:23]2[NH:22][C:7]([CH:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[N:29][C:28]=2[N:27]([CH2:30][CH2:31][CH3:32])[C:26]1=[O:33])[CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 219302Oxane-4-carboxylic acidHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 14795477HCID 14795477, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.2 g (0.025 mol) of tetrahydropyran-4-carboxylic acid, 4.0 g (0.025 mol) of carbonyldiimidazole and 85 ml of absolute methylene chloride are stirred for 30 minutes at ambient temperature. After the addition of 5.7 g (0.025 mol) of 5,6-diamino-1,3-dipropyluracil, the mixture is stirred for 4 hours at ambient temperature and then evaporated down in vacuo. The residue is combined with 130 ml of water and 11.6 g of calcium hydroxide, stirred for 30 minutes at 80° C. and, after cooling, acidified with conc. HCl whilst cooling with ice. The mixture is extracted with ethyl acetate and the organic phase is dried and evaporated. Chromatography of the crystalline residue on silica gel (CH2Cl2CH3OH 99:1) yields 1.7 g of the title compound in the form of white crystals (15% of theory), m.p. 171°-172° C.

Workup

  1. customevaporated down in vacuo
  2. stirringstirred for 30 minutes at 80° C.
  3. temperatureafter cooling
  4. temperaturewhilst cooling with ice
  5. extractionThe mixture is extracted with ethyl acetate
  6. customthe organic phase is dried
  7. customevaporated

Sources & evidence

ORD record
ord-1c28ee9d549f4e999e88e815d1bc97d9
Source dataset
uspto-grants-1996_07
Patent number
US05532368

Reaction notes

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