Acetic Acid → 2-(((3aR,4S,6R,6aS)-6-(7-Chloro-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanol

HRID 1045072Notes

Reaction equation

HRID 1045072 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][C@H:14]2[C@@H:18]3[O:19][C:20]([CH3:23])([CH3:22])[O:21][C@@H:17]3[C@@H:16]([O:24][CH2:25][CH2:26][OH:27])[CH2:15]2)=[N:4][C:5]([S:9][CH2:10][CH2:11][CH3:12])=[N:6][C:7]=1[Cl:8].[N:28]([O-])=O.[Na+].C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.C1(C)C=CC=CC=1>[Cl:8][C:7]1[C:2]2[N:1]=[N:28][N:13]([C@H:14]3[C@@H:18]4[O:19][C:20]([CH3:22])([CH3:23])[O:21][C@@H:17]4[C@@H:16]([O:24][CH2:25][CH2:26][OH:27])[CH2:15]3)[C:3]=2[N:4]=[C:5]([S:9][CH2:10][CH2:11][CH3:12])[N:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 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 210357742-(((3aR,4S,6R,6aS)-6-(7-Chloro-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

2-[((3aR,4S,6R,6aS)-6-{[5-Amino-6-chloro-2-(propylthio)pyrimidin-4-yl]amino}-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]ethanol (320 kg) and sodium nitrite (61 kg) were dissolved in a mixture of water (224 kg) and toluene (1450 kg) at room temperature. Acetic acid (276 kg) was charged with a rate that kept the temperature of the reaction ≦30° C. After full conversion was reached (≧99.9%), potassium carbonate (317 kg) dissolved in water (640 kg) was added to the reaction solution. After the extraction the water layer was separated off and the organic layer was used in the next step.

Workup

  1. customthe temperature of the reaction ≦30° C
  2. additionwas added to the reaction solution
  3. extractionAfter the extraction the water layer
  4. customwas separated off

Sources & evidence

ORD record
ord-8bdf4e27ff264de085a152cdce1350e3
Source dataset
uspto-grants-2013_10
Patent number
US08563755B2

Reaction notes

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