5-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazole → HCID 86296050, compound

HRID 2179108Notes

Reaction equation

HRID 2179108 reaction equation
[CH2:1]([N:8]1[C:12]2[N:13]=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:15]=[C:16]([N:17]3[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18]3)[C:11]=2[N:10]=[N:9]1)[C:2]1C=CC=CC=1.C(C1N=C(N2CC[C@@H](O)C2)C2N=NNC=2N=1)(C)(C)C.C(C1N=C(N2CCC(F)(F)C2)C2C(=NN(CC)N=2)N=1)(C)(C)C.ClC[C:70]1[N:74](C)[N:73]=[N:72][N:71]=1>[Pd]>[C:23]([C:14]1[N:15]=[C:16]([N:17]2[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18]2)[C:11]2[N:10]=[N:9][N:8]([CH2:1][C:2]3[N:71]([CH3:70])[N:72]=[N:73][N:74]=3)[C:12]=2[N:13]=1)([CH3:25])([CH3:26])[CH3:24]

Participants

6

Reactant 4

HCID 122050865-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazoleHCID 715763075-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 86683386(R)-1-(3-Benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-olHCID 178441790HCID 178441790, compound

Product 1

HCID 86296050HCID 86296050, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(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-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine (example 3, step b) with 5-(chloromethyl)-1-methyl-1H-tetrazole. MS (m/e): 359.3 (MH+)

Sources & evidence

ORD record
ord-c9141f036afb4803aac2b92aa30d9e11
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

Loading…