N,N-Diethylaniline → 4-Chloro-1-(2-c-methyl-2,3,5-tri-o-benzoyl-beta-d-ribofuranosyl)imidazo[4,5-d]pyridazine

HRID 402316Notes

Reaction equation

HRID 402316 reaction equation
[CH3:1][C@@:2]1([O:36][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:6]([O:7][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:5]([CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:4][C@H:3]1[N:26]1[C:30]2=[CH:31][N:32]=[N:33][C:34](=O)[C:29]2=[N:28][CH2:27]1.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)[Cl:57]>>[Cl:57][C:34]1[N:33]=[N:32][CH:31]=[C:30]2[N:26]([C@@H:3]3[O:4][C@H:5]([CH2:16][O:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C@@H:6]([O:7][C:8](=[O:15])[C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[C@@:2]3([CH3:1])[O:36][C:37](=[O:44])[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:27]=[N:28][C:29]=12

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24387Phosphorus trichlorideHCID 1317314311-(2-c-Methyl-2,3,5-tri-o-benzoyl-beta-d-ribofuranosyl)imidazo[4,5-d]pyridazin-4-one

Product 1

HCID 577645174-Chloro-1-(2-c-methyl-2,3,5-tri-o-benzoyl-beta-d-ribofuranosyl)imidazo[4,5-d]pyridazine

Procedure

A solution containing the compound from Step A (300 mg, 0.50 mmol), the N,N-diethylaniline (1.2 mL) and freshly distilled phosphorus chloride (24 mL) was stirred at reflux for 1 hour. The reaction mixture was evaporated to dryness. Dichloromethane was added to the residue and the organic layer poured over cracked ice/water. The aqueous layer was extracted with dichloromethane. The organic layer was washed with sodium hydrogenocarbonate 5%, water and was evaporated to dryness. The crude product was purified on silica gel using diethyl ether/petrol ether (1/1) as eluant to give the title compound (295 mg) as a white powder.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe reaction mixture was evaporated to dryness
  3. additionDichloromethane was added to the residue
  4. additionthe organic layer poured over cracked ice/water
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. washThe organic layer was washed with sodium hydrogenocarbonate 5%, water
  7. customwas evaporated to dryness
  8. customThe crude product was purified on silica gel

Sources & evidence

ORD record
ord-4dde310bad37496593d2122a372ac268
Source dataset
uspto-grants-2014_06
Patent number
US08742101B2

Reaction notes

Loading…