Triethylamine → HCID 11059916, compound

HRID 542431Notes

Reaction equation

HRID 542431 reaction equation
C([N:4]1[C:12]2[CH:7]([N:8](C(=O)C)[CH:9]([Cl:17])[N:10](C(=O)C)[C:11]=2Cl)[N:6]([C@@H:21]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[C@H:22]2[OH:23])[CH2:5]1)(=O)C.[C:30]1([CH:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:37][NH2:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>COCCOC>[C:39]1([CH:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:37][NH:38][C:11]2[C:12]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[C:9]([Cl:17])[N:10]=2)[C@@H:21]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[C@H:22]2[OH:23])[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775752,2-DiphenylethylamineHCID 131715099HCID 131715099, compound

Product 1

HCID 11059916HCID 11059916, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2.75 g of triacetyl-2,6-dichloro-9-(β-D-ribofuranosyl)purine (M. J. Robins and B. Uznanski Can. J. Chem., 59, 2601 (1981), J. F. Gerster and R. K. Robins, J. Org. Chem., 31, 3528 (1966)), 1.34 g of 2,2-diphenylethylamine and 0.748 g of triethylamine is stirred at room temperature, under a nitrogen atmosphere for four hours in 50 ml of 1,2-dimethoxyethane (distilled over NaH). The precipitate of Et3N+HCl is filtered and the solvent is evaporated from the filtrate to dryness. The residue is dissolved in 50 ml of methanol saturated with ammonia and stirred at room temperature for three hours. The mixture is evaporated to dryness and the residue is purified by medium pressure liquid chromatography on silica gel using 5% methanol in chloroform as the eluent. Evaporation of the solvent from the pure fractions affords a solid material which is crystallized from a mixture of chloroform-2-propanol (10:1) and hexane yielding N6 -(2,2-diphenylethyl)-2-chloroadenosine, mp 120°- 123° C.

Workup

  1. filtrationThe precipitate of Et3N+HCl is filtered
  2. customthe solvent is evaporated from the filtrate to dryness
  3. dissolutionThe residue is dissolved in 50 ml of methanol saturated with ammonia
  4. customThe mixture is evaporated to dryness
  5. customthe residue is purified by medium pressure liquid chromatography on silica gel using 5% methanol in chloroform as the eluent
  6. customEvaporation of the solvent from the pure fractions
  7. customaffords a solid material which
  8. customis crystallized from a mixture of chloroform-2-propanol (10:1) and hexane

Sources & evidence

ORD record
ord-adf4c35a15e6422d8aebe30b41cc96ef
Source dataset
uspto-grants-1987_04
Patent number
US04657897

Reaction notes

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