alpha-Bromo-o-chlorotoluene → (S)-1-[2-(2-Chloro-benzyl)-5-(2,2,2-trifluoro-ethoxy)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

HRID 2179104Notes

Reaction equation

HRID 2179104 reaction equation
C(C1N=C(N2CCC(F)(F)C2)C2C(=NN(CC)N=2)N=1)(C)(C)C.[F:23][C:24]([F:43])([F:42])[CH2:25][O:26][C:27]1[N:28]=[C:29]([N:36]2[CH2:40][CH2:39][C@H:38]([OH:41])[CH2:37]2)[C:30]2[N:35]=[N:34][NH:33][C:31]=2[N:32]=1.Br[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[Cl:52]>>[Cl:52][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=1[CH2:45][N:34]1[N:33]=[C:31]2[N:32]=[C:27]([O:26][CH2:25][C:24]([F:42])([F:23])[F:43])[N:28]=[C:29]([N:36]3[CH2:40][CH2:39][C@H:38]([OH:41])[CH2:37]3)[C:30]2=[N:35]1

Participants

4

Reactant 3

HCID 11905alpha-Bromo-o-chlorotolueneHCID 715763075-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178521640HCID 178521640, compound

Product 1

HCID 71576188(S)-1-[2-(2-Chloro-benzyl)-5-(2,2,2-trifluoro-ethoxy)-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 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 (S)-1-[5-(2,2,2-Trifluoro-ethoxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol and 1-(bromomethyl)-2-chlorobenzene. MS (m/e): 429.4 (MH+).

Sources & evidence

ORD record
ord-5eb86ff7cc214cab99e03be5c64c80d6
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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