3-Chloro-2-(chloromethyl)pyridine → (S)-1-[5-tert-Butyl-2-(3-chloro-pyridin-2-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

HRID 2179067Notes

Reaction equation

HRID 2179067 reaction equation
C(C1N=C(N2CC[C@H](O)C2)C2C(=NN(CC3C(C)=NON=3)N=2)N=1)(C)(C)C.[C:27]([C:31]1[N:32]=[C:33]([N:40]2[CH2:44][CH2:43][C@H:42]([O:45]C(=O)C(F)(F)F)[CH2:41]2)[C:34]2[N:39]=[N:38][NH:37][C:35]=2[N:36]=1)([CH3:30])([CH3:29])[CH3:28].[Cl:52][C:53]1[C:54]([CH2:59]Cl)=[N:55][CH:56]=[CH:57][CH:58]=1>>[C:27]([C:31]1[N:32]=[C:33]([N:40]2[CH2:44][CH2:43][C@H:42]([OH:45])[CH2:41]2)[C:34]2[C:35](=[N:37][N:38]([CH2:59][C:54]3[C:53]([Cl:52])=[CH:58][CH:57]=[CH:56][N:55]=3)[N:39]=2)[N:36]=1)([CH3:29])([CH3:30])[CH3:28]

Participants

4

Reactant 3

HCID 145171573-Chloro-2-(chloromethyl)pyridineHCID 71575968(S)-1-[5-tert-Butyl-2-(4-methyl-furazan-3-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-olHCID 178441791HCID 178441791, compound

Product 1

HCID 71575970(S)-1-[5-tert-Butyl-2-(3-chloro-pyridin-2-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

Procedure

In analogy to the procedure described for the synthesis of (S)-1-[5-tert-Butyl-2-(4-methyl-furazan-3-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol (example 73), the title compound was prepared from Trifluoro-acetic acid (S)-1-(5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-yl-ester and 3-chloro-2-(chloromethyl)pyridine and isolated as light yellow gum. MS (m/e): 388.3 (MH+).

Workup

  1. customisolated as light yellow gum

Sources & evidence

ORD record
ord-92a8860c6c014299824f36de4d3f885c
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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