Isoamyl Nitrite → (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 923299Notes

Reaction equation

HRID 923299 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][C@@H:14]2[CH2:18][C@H:17]([O:19][CH2:20][CH2:21][OH:22])[C@@H:16]([OH:23])[C@H:15]2[OH:24])=[N:4][C:5]([S:9][CH2:10][CH2:11][CH3:12])=[N:6][C:7]=1[Cl:8].[N:25](OCCC(C)C)=O>C(OCC)(=O)C>[Cl:8][C:7]1[C:2]2[N:1]=[N:25][N:13]([C@@H:14]3[CH2:18][C@H:17]([O:19][CH2:20][CH2:21][OH:22])[C@@H:16]([OH:23])[C@H:15]3[OH:24])[C:3]=2[N:4]=[C:5]([S:9][CH2:10][CH2:11][CH3:12])[N:6]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 71609773(1S,2S,3R,5S)-3-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol

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 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a stirring solution of (1S,2S,3R,5S)-3-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol (OLACINA; 0.38 g, 1 mmol) in ethyl acetate (7 mL) was added isopentyl nitrite (0.16 mL, 1.2 mmol). The reaction mixture was stirred for 1 h at 65° C. and then evaporated under reduced pressure to give a reddish powder which was recrystallized from a mixture of methyl tert-butyl ether/n-hexane to give CLTOL as a crystalline product (0.31 g, 80% yield): 99 area % by HPLC.

Workup

  1. customevaporated under reduced pressure
  2. customto give a reddish powder which
  3. customwas recrystallized from a mixture of methyl tert-butyl ether/n-hexane

Sources & evidence

ORD record
ord-41bc611dab6a40c482b66e14747f13e4
Source dataset
uspto-grants-2016_03
Patent number
US09278972B2

Reaction notes

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