1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 135610070, compound

HRID 2056268Notes

Reaction equation

HRID 2056268 reaction equation
[C:1]([C:4]1[O:8][N:7]=[C:6]([O:9][CH2:10][C:11]([O:13]CC)=[O:12])[CH:5]=1)(O)=O.CCN=C=NCCCN(C)C.[CH2:27]([N:30]1[C:37]([NH2:38])=[C:36]([NH2:39])[C:34](=[O:35])[N:33]([CH2:40][CH2:41][CH3:42])[C:31]1=[O:32])[CH2:28][CH3:29]>CO>[CH2:40]([N:33]1[C:34](=[O:35])[C:36]2[NH:39][C:1]([C:4]3[O:8][N:7]=[C:6]([O:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=3)=[N:38][C:37]=2[N:30]([CH2:27][CH2:28][CH3:29])[C:31]1=[O:32])[CH2:41][CH3:42]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 58846560HCID 58846560, compound

Product 1

HCID 135610070HCID 135610070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of ethyl (5-carboxyisoxazol-3-yl)oxyacetate (0.5 mmol) and EDCI (0.5 mmol) in methanol (20 mL) was added a solution of 1,3-dipropyl-5,6-diaminouracil (0.5 mmol), dissolved in methanol (20 mL). The mixture was stirred at room temperature for two hours, the solvent was then removed in vacuo, water added, and the solid that formed was collected by filtration and washed with additional cold water. The intermediate amide was heated in 20 mL of 2.5 N NaOH at 70° C. for 30 minutes to afford the desired 2-[5-(1,3-dipropyl-xanthin-8-yl)-isoxazol-3-yloxy]acetic acid.

Workup

  1. customthe solvent was then removed in vacuo, water
  2. additionadded
  3. customthe solid that formed
  4. filtrationwas collected by filtration
  5. washwashed with additional cold water
  6. temperatureThe intermediate amide was heated in 20 mL of 2.5 N NaOH at 70° C. for 30 minutes

Sources & evidence

ORD record
ord-f404d52827924dd3a81d0a51ce07c851
Source dataset
uspto-grants-2008_02
Patent number
US07335655B2

Reaction notes

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