5-tert-Butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine → HCID 86683386, compound

HRID 400977Notes

Reaction equation

HRID 400977 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]=3Cl)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N1C2N=C(C(C)(C)C)N=C(Cl)C=2N=N1)C1C=CC=CC=1.N1CC[C@@H](O)C1.C(N1C2N=C(C(C)(C)C)N=C(N3CC[C@@H](O)C3)C=2N=N1)C1C=CC=CC=1.C(C1N=C(N2CC[C@@H](O)C2)C2N=NN(CC3N(C)N=NN=3)C=2N=1)(C)(C)C.C(C1N=C(N2CC[C@@H](O)C2)C2N=NNC=2N=1)(C)(C)C.C(C1N=C(N2CCC(F)(F)C2)C2N=NN(CC)C=2N=1)(C)(C)C.ClCC1N(C)N=NN=1>[Pd]>[CH2:14]([N:11]1[C:9]2[N:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:6]=[C:7]([N:22]3[CH2:27][CH2:26][C@@H:24]([OH:25])[CH2:23]3)[C:8]=2[N:13]=[N:12]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

9

Reactant 7

HCID 14339535-tert-Butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 2759337(R)-3-PyrrolidinolHCID 122050865-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazoleHCID 715582055-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 866833853-Benzyl-5-tert-butyl-7-chloro-triazolo[4,5-d]pyrimidineHCID 86683387HCID 86683387, compoundHCID 178441790HCID 178441790, compound

Product 1

HCID 86683386HCID 86683386, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In analogy to the procedure described for the synthesis of 5-tert-butyl-3-(2-chlorobenzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 1, step c), the title compound was prepared from 3-benzyl-5-tert-butyl-7-chloro-triazolo[4,5-d]pyrimidine and (R)-pyrrolidin-3-ol and isolated as white foam. MS (m/e): 352.4 (MH+). b)(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 (R)-1-(3-Benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-ol was hydrogenated over Pd/C and the resulting (R)-1-(5-tert-Butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-ol was reacted 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), with 5-(chloromethyl)-1-methyl-1H-tetrazole and isolated as white solid. MS (m/e): 359.2 (MH+).

Workup

  1. customisolated as white foam
  2. customisolated as white solid

Sources & evidence

ORD record
ord-69a0245d45814db391d0d791eec2956c
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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