Pyridinium chloride → HCID 86723475, compound

HRID 2201240Notes

Reaction equation

HRID 2201240 reaction equation
Cl.N1C=CC=CC=1.[Cl:8][C:9]1[N:10]=[C:11]([C:14](=O)[CH2:15][CH2:16][CH2:17][N:18]2[C:26]([C:27]3[CH:31]=[CH:30][N:29]([CH3:32])[N:28]=3)=[C:25]3[C:20]([N:21]([CH3:36])[C:22](=[O:35])[N:23]([CH3:34])[C:24]3=[O:33])=[CH:19]2)[S:12][CH:13]=1>CO.O.C(Cl)(Cl)Cl>[Cl:8][C:9]1[N:10]=[C:11]([C:14]2[C:19]3[N:18]([C:26]([C:27]4[CH:31]=[CH:30][N:29]([CH3:32])[N:28]=4)=[C:25]4[C:24](=[O:33])[N:23]([CH3:34])[C:22](=[O:35])[N:21]([CH3:36])[C:20]4=3)[CH2:17][CH2:16][CH:15]=2)[S:12][CH:13]=1

Participants

6

Reactant 2

HCID 10176127Pyridinium chlorideHCID 86723476HCID 86723476, compound

Product 1

HCID 86723475HCID 86723475, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Pyridine hydrochloride (6.02 g, 52.1 mmol) was added to a suspension of 6-(4-(4-chlorothiazol-2-yl)-4-oxobutyl)-1,3-dimethyl-5-(1-methyl-1H-pyrazol-3-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (2.33 g, 5.21 mmol) in methanol (82 ml) and water (8.17 ml) and the mixture stirred at room temperature for 3 days. The mixture was then diluted with chloroform (300 ml), washed with 1M HCl(aq) (3×100 ml) and saturated NaHCO3(aq) (100 ml). The organic phase was passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 50-80% EtOAc/hexane afforded a crude material which was triturated with methanol to afford the title compound.

Workup

  1. washwashed with 1M HCl(aq) (3×100 ml) and saturated NaHCO3(aq) (100 ml)
  2. customevaporated under vacuum
  3. customPurification by chromatography on silica
  4. washeluting with 50-80% EtOAc/hexane
  5. customafforded a crude material which
  6. customwas triturated with methanol

Sources & evidence

ORD record
ord-2a5c93bbdcce45f7801f60e1d97e4b24
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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