Ethanol → HCID 131714931, compound

HRID 2290197Notes

Reaction equation

HRID 2290197 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.C([N:22]([CH2:25][CH3:26])CC)C.[OH2:27].[CH2:28]([OH:30])C>>[OH:27][CH:26]([CH2:28][OH:30])[CH2:25][NH:22][C:5]1[C:4]2[N:8]=[CH:9][N:10]([C:3]=2[N:2]=[CH:1][N:6]=1)[C@@H:11]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@@H:12]1[OH:19]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 8471TriethylamineHCID 930036-Chloropurine riboside

Product 1

HCID 131714931HCID 131714931, compound

Procedure

6-chloropurineriboside (5.8 g, 20 mmol, 2,3-propylaminediol (1.82 g, 20 mmol) and triethylamine (2.02 g, 20 mmol) were combined in 250 ml ethanol and refluxed for 18 hours. Removal of the ethanol gave a viscous syrup. Refluxing ethanol was added to the syrup sufficient to dissolve it, then allowed to cool and stand at 0° for 24 hours. The resulting crystals were filtered and dried, yielding 3.6 g (53%) m.p. 164°-165° analysis for C13H19N5O6) Calcd: C=45.74, H=5.61, N=20.52; Found: C=45.93, H=5.49, N=20.63, H2O 0.70.

Workup

  1. temperaturerefluxed for 18 hours
  2. customRemoval of the ethanol
  3. customgave a viscous syrup
  4. dissolutionto dissolve it
  5. temperatureto cool
  6. filtrationThe resulting crystals were filtered
  7. customdried
  8. customyielding 3.6 g (53%) m.p. 164°-165° analysis for C13H19N5O6) Calcd

Sources & evidence

ORD record
ord-a1428cf418ee4d749f84083fd710f4d4
Source dataset
uspto-grants-1986_10
Patent number
US04616003

Reaction notes

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