Triethylamine → HCID 70401066, compound

HRID 2119123Notes

Reaction equation

HRID 2119123 reaction equation
[CH:1]1[N:6]=[C:5](Cl)[C:4]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[C:3]=2[N:2]=1.Cl.[CH3:21][O:22][C:23]1[CH:32]=[C:31]2[C:26]([CH2:27][CH:28]([NH2:33])[CH2:29][O:30]2)=[CH:25][CH:24]=1.C([N:36](CC)CC)C>C(O)C>[CH3:21][O:22][C:23]1[CH:32]=[C:31]2[C:26]([CH2:27][CH:28]([NH:33][NH:36][C:5]3[C:4]4[N:8]=[CH:9][N:10]([C:3]=4[N:2]=[CH:1][N:6]=3)[C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[CH2:29][O:30]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 30416007-Methoxy-3,4-dihydro-2H-1-benzopyran-3-amine--hydrogen chloride (1/1)

Product 1

HCID 70401066HCID 70401066, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.56 g 6-chloropurine riboside, 0.5 g 7-methoxy-3-chromanylamine hydrochloride, and 0.48 g of triethylamine is refluxed in 25 ml ethanol under nitrogen for 20 hrs. Solvent is evaporated to dryness and residue is treated with cold water. The clear aqueous solution is decanted off, residue is dissolved in ethanol and volatiles are evaporated under vacuo. The crude solid is purified by flash-chromatography on silica-gel using 5% methanolchloroform as an eluant. Evaporation of solvent from pure fractions followed by crystallization from CHCl3 -hexane affords 0.35 g (42%) of N6 -[7-methoxy-3-chromanylamino]adenosine having a melting point of 205°-207° C.

Workup

  1. customSolvent is evaporated to dryness and residue
  2. additionis treated with cold water
  3. customThe clear aqueous solution is decanted off
  4. dissolutionresidue is dissolved in ethanol
  5. customvolatiles are evaporated under vacuo
  6. customThe crude solid is purified by flash-chromatography on silica-gel
  7. customEvaporation of solvent from pure fractions
  8. customfollowed by crystallization from CHCl3 -hexane

Sources & evidence

ORD record
ord-3c68b8b8590541d2a70aad080e5b8f78
Source dataset
uspto-grants-1987_07
Patent number
US04683223

Reaction notes

Loading…