5-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazole → 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

HRID 400978Notes

Reaction equation

HRID 400978 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]([CH2:14][C:15]3[N:19]([CH3:20])[N:18]=[N:17][N:16]=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N1C2N=C(C(C)(C)C)N=C(N3CCC(O)C3)C=2N=N1)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[N:13]=[N:12][N:11]([CH2:14][C:15]3[N:19]([CH3:20])[N:18]=[N:17][N:16]=3)[C:9]=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 862960471-(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

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 219, step 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): 358.4 (MH+).

Workup

  1. customisolated as light yellow oil

Sources & evidence

ORD record
ord-6ac940a224a14f4c9124e95d1ab1cb20
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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