((5,8-Dimethyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)methyl)triphenylphosphonium chloride → 5,8-dimethyl-2-{(E)-2-[2-methyl-5-(2-methyl-pyrrolidin-1-yl)-2H-[1,2,4]triazol-3-yl]-vinyl}-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1055018Notes

Reaction equation

HRID 1055018 reaction equation
[Cl-].[CH3:2][C:3]1[N:8]2[N:9]=[C:10]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=[C:7]2[C:6]([CH3:32])=[CH:5][N:4]=1.[CH3:33][N:34]1[C:38]([CH:39]=O)=[N:37][C:36]([N:41]2[CH2:45][CH2:44][CH2:43][CH:42]2[CH3:46])=[N:35]1>>[CH3:2][C:3]1[N:8]2[N:9]=[C:10](/[CH:12]=[CH:39]/[C:38]3[N:34]([CH3:33])[N:35]=[C:36]([N:41]4[CH2:45][CH2:44][CH2:43][CH:42]4[CH3:46])[N:37]=3)[N:11]=[C:7]2[C:6]([CH3:32])=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 88152107((5,8-Dimethyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)methyl)triphenylphosphonium chlorideHCID 900170411-methyl-3-(2-methylpyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde

Product 1

HCID 900174875,8-dimethyl-2-{(E)-2-[2-methyl-5-(2-methyl-pyrrolidin-1-yl)-2H-[1,2,4]triazol-3-yl]-vinyl}-[1,2,4]triazolo[1,5-c]pyrimidineYield 73.6%

Procedure

Was prepared in the same manner as described in Example 49e) using ((5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)methyl)triphenylphosphonium chloride (350 mg, 763 μmol, Eq: 1.00) and 1-methyl-3-(2-methylpyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (148 mg, 763 μmol, Eq: 1.00) affording 5,8-dimethyl-2-{(E)-2-[2-methyl-5-(2-methyl-pyrrolidin-1-yl)-2H-[1,2,4]triazol-3-yl]-vinyl}-[1,2,4]triazolo[1,5-c]pyrimidine (190 mg, 73.6%) as a bright yellow solid. MS: m/z=339.5 (M+H+)

Workup

  1. customWas prepared in the same manner

Sources & evidence

ORD record
ord-266912d2da694bec843eb12300f279f2
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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