Diethyl Ether → HCID 136166729, compound

HRID 1534937Notes

Reaction equation

HRID 1534937 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][OH:7].[O:8]=[C:9]1[NH:17][CH:16]=[N:15][C:14]2[N:13]([CH2:18][CH2:19][C:20](OCC)=[O:21])[CH:12]=[N:11][C:10]1=2.CCOCC>CO>[O:8]=[C:9]1[NH:17][CH:16]=[N:15][C:14]2[N:13]([CH2:18][CH2:19][C:20]([NH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][OH:7])=[O:21])[CH:12]=[N:11][C:10]1=2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 136166729HCID 136166729, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.500 (4,80 mmol) 2-(2-aminoethylamino)ethanol and 0.250 g (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) were heated at 120° C. with stirring in a 10 ml round bottom flask for one hour. The reaction mixture was chromatographed on a 15 g silica-gel column using an eluant of 60% methanol/40% ethyl acetate. After 200 ml of solvent had passed through column, the eluant was changed to 80% methanol/20% ethyl acetate and finally to 100% methanol. The fractions containing the product were combined and evaporated to yield a colorless oil. The oil was treated with 50 ml ether and 5 ml methanol and was agitated with a spatula. The oil was allowed to stand overnight and the resulting white solid was obtained by filtration (120 mg). The solid was washed with ether and was found to be somewhat hygroscopic. Yield: 38%.

Workup

  1. customThe reaction mixture was chromatographed on a 15 g silica-gel column
  2. additionThe fractions containing the product
  3. customevaporated
  4. customto yield a colorless oil
  5. stirringwas agitated with a spatula
  6. waitto stand overnight
  7. customthe resulting white solid was obtained by filtration (120 mg)
  8. washThe solid was washed with ether

Sources & evidence

ORD record
ord-3c37d91fbdda407cbb8a54eb82208855
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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