5-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazole → 1-[5-tert-Butyl-2-(1-methyl-1H-tetrazol-5-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

HRID 2179110Notes

Reaction equation

HRID 2179110 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[N:13]=[N:12][N:11](CC3N(C)N=NN=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C([N:34]1[C:38]2[N:39]=[C:40](C(C)(C)C)N=C(N3CCC(O)C3)[C:37]=2[N:36]=[N:35]1)C1C=CC=CC=1.ClCC1N(C)N=NN=1>>[C:1]([C:5]1[N:6]=[C:7]([N:21]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22]2)[C:8]2[C:9](=[N:11][N:12]([CH2:37][C:38]3[N:39]([CH3:40])[N:36]=[N:35][N:34]=3)[N:13]=2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 122050865-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazoleHCID 86296050HCID 86296050, compoundHCID 866833891-(3-Benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-ol

Product 1

HCID 895865571-[5-tert-Butyl-2-(1-methyl-1H-tetrazol-5-ylmethyl)-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 (R)-1-(5-tert-butyl-3-((1-methyl-1H-tetrazol-5-yl)methyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)pyrrolidin-3-ol (example 113, b) 1-(3-Benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-ol was hydrogenated and subsequently reacted with 5-(chloromethyl)-1-methyl-1H-tetrazole and isolated as light yellow oil. MS (m/e): 359.3 (MH+).

Workup

  1. customisolated as light yellow oil

Sources & evidence

ORD record
ord-302c9e4031804125a39993aac8350cd2
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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