1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde → 5,8-dimethyl-2-[(E)-2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1054992Notes

Reaction equation

HRID 1054992 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[N:5][C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:3]1.[Cl-].[CH3:15][C:16]1[N:21]2[N:22]=[C:23]([CH2:25][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:24]=[C:20]2[C:19]([CH3:45])=[CH:18][N:17]=1>>[CH3:15][C:16]1[N:21]2[N:22]=[C:23](/[CH:25]=[CH:7]/[C:6]3[N:2]([CH3:1])[N:3]=[C:4]([N:9]4[CH2:13][CH2:12][CH2:11][CH2:10]4)[N:5]=3)[N:24]=[C:20]2[C:19]([CH3:45])=[CH:18][N:17]=1

Participants

3

Reactant 2

HCID 838754401-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehydeHCID 88152107((5,8-Dimethyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)methyl)triphenylphosphonium chloride

Product 1

HCID 900182185,8-dimethyl-2-[(E)-2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-[1,2,4]triazolo[1,5-c]pyrimidineYield 50.1%

Procedure

Was prepared in the same manner as described in Example 81a) using 1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (30 mg, 166 μmol, Eq: 1.00) and ((5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)methyl)triphenylphosphonium chloride (76.4 mg, 166 μmol, Eq: 1.00) (prepared as described in WO2011150156, pp 123-125, Expl. 24 g) affording 5,8-dimethyl-2-[(E)-2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-[1,2,4]triazolo[1,5-c]pyrimidine (27 mg, 50.0%) as light yellow amorphous. MS: m/z=325.6 (M+H+)

Workup

  1. customWas prepared in the same manner
  2. customprepared

Sources & evidence

ORD record
ord-847544f4eb054e0783b1aadaa2d9e4f9
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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