5-tert-Butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine → (3S,4R)-1-[5-tert-Butyl-3-(2-chloro-benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidine-3,4-diol

HRID 400846Notes

Reaction equation

HRID 400846 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(Cl)C2N=NN(CC3C=CC=CC=3Cl)C=2N=1)(C)(C)C.N1C[C@H]([OH:55])[C@H](O)C1>>[C:1]([C:5]1[N:6]=[C:7]([N:22]2[CH2:27][C@@H:26]([OH:55])[C@@H:24]([OH:25])[CH2:23]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 14339535-tert-Butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 13329882(3R,4S)-pyrrolidine-3,4-diolHCID 866832845-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 86683298(3S,4R)-1-[5-tert-Butyl-3-(2-chloro-benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidine-3,4-diol

Procedure

In analogy to the procedure described for the synthesis of 5-tert-butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 1, step c), the title compound was prepared from 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and (3R,4S)-pyrrolidine-3,4-diol and isolated as light-yellow gum (10.3 mg, 54%). MS (m/e): 403.4 (MH+).

Sources & evidence

ORD record
ord-6d2d63bc37d940f3b2d5ea78c976e2d3
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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