Triethylamine → HCID 70418443, compound

HRID 542433Notes

Reaction equation

HRID 542433 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13].Cl.[C:21]1([C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([CH3:30])[CH2:28][NH2:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>CN(C)C=O>[C:31]1([C:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([CH3:30])[CH2:28][NH:29][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[CH:9][N:10]=2)[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 30847982,2-Diphenylpropan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 70418443HCID 70418443, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-9-β-D-ribofuranosylpurine (2.32 g, 8.09 mmol), 2,2-diphenylpropylamine hydrochloride (2.01 g, 100 mol%) and triethylamine (2.3 mL, 204 mol%) in N,N-dimethylformamide (30 mL) is stirred under nitrogen at room temperature for 19 days, filtered, the solid is washed with ether, and the filtrate is evaporated to an oil. The oil is purified by column chromatography over silica gel, eluting with 5/1 chloroform/methanol, and the appropriate fractions are evaporated to afford N6 -(2,2-diphenylpropyl)adenosine as a foam which retains one-half mole of N,N-dimethylformamide.

Workup

  1. filtrationfiltered
  2. washthe solid is washed with ether
  3. customthe filtrate is evaporated to an oil
  4. customThe oil is purified by column chromatography over silica gel
  5. washeluting with 5/1 chloroform/methanol
  6. customthe appropriate fractions are evaporated

Sources & evidence

ORD record
ord-87da492c914e43b3983817cf1383a942
Source dataset
uspto-grants-1987_04
Patent number
US04657897

Reaction notes

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