(S)-(+)-3-Hydroxytetrahydrofuran → 5-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-(R)-tetrahydro-furan-3-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 2173581Notes

Reaction equation

HRID 2173581 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.[O:43]1CC[C@H:45](O)[CH2:44]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]([C@@H:14]3[CH2:45][CH2:44][O:43][CH2:15]3)[C:9]=2[N:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 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 866833135-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-(R)-tetrahydro-furan-3-yl-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 (S)-tetrahydrofuran-3-ol and isolated as colorless gum. MS(m/e): 353.3 (MH+).

Workup

  1. customisolated as colorless gum

Sources & evidence

ORD record
ord-86ced83f13e54e268f000da866b64e6e
Source dataset
uspto-grants-2015_06
Patent number
US09056866B2

Reaction notes

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