3-Chloro-2-(chloromethyl)pyridine → 5-tert-Butyl-2-(3-chloro-pyridin-2-ylmethyl)-7-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-2H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 2179099Notes

Reaction equation

HRID 2179099 reaction equation
C(C1N=C(N2CCC(F)(F)C2)C2C(=NN(CC)N=2)N=1)(C)(C)C.[C:23]([C:27]1[N:28]=[C:29]([N:36]2[CH2:42][C:38]3([CH2:41][O:40][CH2:39]3)[CH2:37]2)[C:30]2[N:35]=[N:34][NH:33][C:31]=2[N:32]=1)([CH3:26])([CH3:25])[CH3:24].[Cl:43][C:44]1[C:45]([CH2:50]Cl)=[N:46][CH:47]=[CH:48][CH:49]=1>>[C:23]([C:27]1[N:28]=[C:29]([N:36]2[CH2:37][C:38]3([CH2:39][O:40][CH2:41]3)[CH2:42]2)[C:30]2[C:31](=[N:33][N:34]([CH2:50][C:45]3[C:44]([Cl:43])=[CH:49][CH:48]=[CH:47][N:46]=3)[N:35]=2)[N:32]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 3

HCID 145171573-Chloro-2-(chloromethyl)pyridineHCID 715763075-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178441781HCID 178441781, compound

Product 1

HCID 715761875-tert-Butyl-2-(3-chloro-pyridin-2-ylmethyl)-7-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-2H-[1,2,3]triazolo[4,5-d]pyrimidine

Procedure

In analogy to the procedure described for the synthesis of 5-tert-butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine (example 3, step b), the title compound was prepared from 5-tert-Butyl-7-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and 3-chloro-2-(chloromethyl)pyridine and isolated as light brown gum. MS (m/e): 400.3 (MH+).

Workup

  1. customisolated as light brown gum

Sources & evidence

ORD record
ord-3ff75b5d18be4719887f853dd49c4df1
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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