3-(Chloromethyl)-5-methyl-1,2,4-oxadiazole → 5-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-(5-methyl-[1,2,4]oxadiazol-3-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 400919

Reaction equation

HRID 400919 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:16]2[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][CH3:15])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(N2CCC(F)(F)C2)C2N=NNC=2N=1)(C)(C)C.ClCC1[N:49]=[C:48]([CH3:50])[O:47][N:46]=1>>[C:1]([C:5]1[N:6]=[C:7]([N:16]2[CH2:20][CH2:19][C:18]([F:21])([F:22])[CH2:17]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[N:49]=[C:48]([CH3:50])[O:47][N:46]=3)[C:9]=2[N:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 3021573-(Chloromethyl)-5-methyl-1,2,4-oxadiazoleHCID 715582055-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178441789HCID 178441789, compound

Product 1

HCID 866833275-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-(5-methyl-[1,2,4]oxadiazol-3-ylmethyl)-3H-[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-difluoropyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 61), the title compound was prepared from 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and 3-(chloromethyl)-5-methyl-1,2,4-oxadiazole and isolated as yellow gum. MS (m/e): 379.3 (MH+).

Workup

  1. customisolated as yellow gum

Sources & evidence

ORD record
ord-cadabe181b254276bb2eb9a0908e4662
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Linked notes

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