Triethylamine → HCID 66696639, compound

HRID 641151Notes

Reaction equation

HRID 641151 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.[NH2:20][CH:21]1[CH2:25][CH2:24][O:23][CH2:22]1.C(N(CC)CC)C>CO>[OH:17][CH2:16][C@@H:14]1[C@H:13]([OH:18])[C@H:12]([OH:19])[C@H:11]([N:10]2[CH:9]=[N:8][C:4]3[C:3]2=[N:2][CH:1]=[N:6][C:5]=3[NH:20][CH:21]2[CH2:25][CH2:24][O:23][CH2:22]2)[O:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 3365553Oxolan-3-amine

Product 1

HCID 66696639HCID 66696639, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-chloropurine riboside (0.5 gm, 1.74 mmol), 3-aminotetrahydrofuran (0.325 gm, 2.6 mmol) and triethylamine (0.73 ml, 5.22 mmol) in methanol (10 ml) was heated to 80° C. for 40 hours. The mixture was cooled and concentrated under reduced pressure. The residue was chromatographed on a short column of silica gel, eluting with methylene chloride/methanol/propylamine (90/10/1). The fractions containing the product were combined and concentrated under reduced pressure. The residue was chromatographed on a chromatotron (2 mm plate, 92.5/7.5/1, methylene chloride/methanol/propylamine). The resulting white solid was recrystallized from methanol/ethyl acetate to give 0.27 gm of (4S,2R,3R,5R)-2-hydroxymethyl-5-[6-(tetrahydrofuran-3-ylamino)-purin-9-yl]-tetrahydrofuran-3,4-diol as white crystals (mp 128° C.-130° C.).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed on a short column of silica gel
  4. washeluting with methylene chloride/methanol/propylamine (90/10/1)
  5. additionThe fractions containing the product
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a chromatotron (2 mm plate, 92.5/7.5/1, methylene chloride/methanol/propylamine)
  8. customThe resulting white solid was recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-88f52d8e3e37465d9923c348a8406624
Source dataset
uspto-grants-2010_04
Patent number
US07696181B2

Reaction notes

Loading…