Hydrochloric Acid → (1S,2S,3R,5S)-3-(7-Chloro-5-(Propylthio)-3H-[1,2,3]Triazolo[4,5-d]Pyrimidin-3-Yl)-5-(2-Hydroxyethoxy)Cyclopentane-1,2-Diol

HRID 589817Notes

Reaction equation

HRID 589817 reaction equation
Cl.[NH2:2][C:3]1[C:4]([NH:14][C@H:15]2[C@@H:19]3[O:20]C(C)(C)[O:22][C@@H:18]3[C@@H:17]([O:25][CH2:26][CH2:27][OH:28])[CH2:16]2)=[N:5][C:6]([S:10][CH2:11][CH2:12][CH3:13])=[N:7][C:8]=1[Cl:9].[N:29]([O-])=O.[Na+]>O>[Cl:9][C:8]1[C:3]2[N:2]=[N:29][N:14]([C@@H:15]3[CH2:16][C@H:17]([O:25][CH2:26][CH2:27][OH:28])[C@@H:18]([OH:22])[C@H:19]3[OH:20])[C:4]=2[N:5]=[C:6]([S:10][CH2:11][CH2:12][CH3:13])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 102021862-(((3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanolHCID 23668193Sodium Nitrite

Product 1

HCID 71609809(1S,2S,3R,5S)-3-(7-Chloro-5-(Propylthio)-3H-[1,2,3]Triazolo[4,5-d]Pyrimidin-3-Yl)-5-(2-Hydroxyethoxy)Cyclopentane-1,2-DiolYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with water (20 mL) and concentrated hydrochloric acid (35%, 1.5 mL). To this, 2-(((3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol (5 g) was added and the mixture was stirred for clear solution. To this mixture, aqueous sodium nitrite solution (0.86 g in 5 mL) was slowly added at room temperature over a period of 15 minutes and mixture was stirred for about 30 minutes and completion of reaction was monitored by TLC. The solid obtained is isolated by filtration and washed with water (5 mL) and dried under vacuum to afford the title compound in about 80% yield.

Workup

  1. stirringmixture was stirred for about 30 minutes
  2. customcompletion of reaction
  3. customThe solid obtained
  4. customis isolated by filtration
  5. washwashed with water (5 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-354ff8d2736741a89d6dbabd8e30e0fc
Source dataset
uspto-grants-2016_01
Patent number
US09233966B2

Reaction notes

Loading…