Triethylamine → HCID 18725654, compound

HRID 411852Notes

Reaction equation

HRID 411852 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[CH2:3]1.[CH:17]1[N:22]=[C:21](Cl)[C:20]2[N:24]=[CH:25][N:26]([C@@H:27]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:29]([OH:34])[C@H:28]3[OH:35])[C:19]=2[N:18]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(O)(C)C.C(Cl)Cl.C(O)C>[OH:33][CH2:32][C@@H:30]1[C@@H:29]([OH:34])[C@@H:28]([OH:35])[C@H:27]([N:26]2[CH:25]=[N:24][C:20]3[C:19]2=[N:18][CH:17]=[N:22][C:21]=3[NH:1][C@@H:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=3)[CH2:3]2)[O:31]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 516892Sodium BicarbonateHCID 11401990HCID 11401990, compound

Product 1

HCID 18725654HCID 18725654, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

267 mg 2-[(3R)-3-aminopyrrolidin-1-yl]-5-trifluoromethylpyridine, 331 mg 6-chloropurineriboside, 233 mg triethylamine, and 0.5 mL ethanol are combined and heated in a sealed vessel at 100° C. for about 5 hours. The mixture is cooled, partioned between methylene chloride (with some isopropyl alcohol added) and sodium bicarbonate. The organic layer is washed with brine, dried over magnesium sulfate, evaporated, and the residue purified by flash chromatography, eluting with 5% methanol in methylene chloride, to give (2R,3S,4R,5R)-2-hydroxymethyl-5-[6-[1-(5-trifluoromethylpyridin-2-yl)-pyrrolidin-3(R)-ylamino]purin-9-yl]tetrahydrofuran-3,4-diol, as the hemihydrate, m.p. 166-170° C.

Workup

  1. temperatureThe mixture is cooled
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customthe residue purified by flash chromatography
  6. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-f6c90f79a210403aa530795ef9fb456f
Source dataset
uspto-grants-2003_05
Patent number
US06559313B2

Reaction notes

Loading…