Cyclopentanecarboxylic acid → HCID 14978323, compound

HRID 2401306Notes

Reaction equation

HRID 2401306 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[N:4]([CH2:10][CH2:11][CH3:12])[C:5](=[O:9])[NH:6][C:7]=1[NH2:8].[CH:14]1([C:19](O)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl.C(N=C=NCCCN(C)C)C>CO>[NH2:8][C:7]1[NH:6][C:5](=[O:9])[N:4]([CH2:10][CH2:11][CH3:12])[C:3](=[O:13])[C:2]=1[NH:1][C:19]([CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:20]

Participants

5

Reactant 3

HCID 18840Cyclopentanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109542025,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 14978323HCID 14978323, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5,6-diamino-3-propyl-1H-pyrimidine-2,4-dione (0.6 g, 2.72 mmol) in methanol (50 ml) was added cyclopentane carboxylic acid (0.310 g, 2.72 mmol). The reaction mixture was cooled to 0° C. and then 1-ethyl-3(3′-dimethylaminopropyl) carbodiimide hydrochloride (EDCI.HCl) (0.78 g, 4.1 mmol) was added. The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water. The solid was filtered and washed thoroughly with water followed by diethyl ether. The product obtained was dried under high vacuum. The crude product (0.40 g) was used for the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. filtrationThe solid was filtered
  5. washwashed thoroughly with water
  6. customThe product obtained
  7. customwas dried under high vacuum
  8. customThe crude product (0.40 g) was used for the next step without further purification

Sources & evidence

ORD record
ord-fcb481489b4f437d887a7f6d1cd8c772
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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