1-(Bromomethyl)-2-methanesulfonylbenzene → (S)-1-[5-tert-Butyl-2-(2-methanesulfonyl-benzyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

HRID 2179072Notes

Reaction equation

HRID 2179072 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:21]2[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22]2)[C:8]2[C:9](=[N:11][N:12]([CH2:14][C:15]3[C:19]([CH3:20])=NON=3)[N:13]=2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(N2CC[C@H](OC(=O)C(F)(F)F)C2)C2N=NNC=2N=1)(C)(C)C.Br[CH2:53][C:54]1C=CC=C[C:55]=1[S:60]([CH3:63])(=[O:62])=[O:61]>>[C:1]([C:5]1[N:6]=[C:7]([N:21]2[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22]2)[C:8]2[C:9](=[N:11][N:12]([CH2:14][C:15]3[CH:19]=[CH:20][CH:53]=[CH:54][C:55]=3[S:60]([CH3:63])(=[O:62])=[O:61])[N:13]=2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 189224741-(Bromomethyl)-2-methanesulfonylbenzeneHCID 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 71576036(S)-1-[5-tert-Butyl-2-(2-methanesulfonyl-benzyl)-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 1-(bromomethyl)-2-(methylsulfonyl)benzene and isolated as white solid. MS (m/e): 431.3 (MH+).

Workup

  1. customisolated as white solid

Sources & evidence

ORD record
ord-6c99f2a129c247d1945f0d7e0cda70b6
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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