1H-1,2,4-Triazole → HCID 178446077, compound

HRID 1787776Notes

Reaction equation

HRID 1787776 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Br[C:9]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:16]2[C:15](=[O:27])[N:14]3[C:28]([CH3:31])=[N:29][N:30]=[C:13]3[N:12]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:11]=2[N:10]=1>CN(C=O)C>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:17]2[C:16]3[C:15](=[O:27])[N:14]4[C:28]([CH3:31])=[N:29][N:30]=[C:13]4[N:12]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:11]=3[N:10]=[C:9]2[N:4]2[CH2:5][NH:6][CH:7]=[N:3]2)=[CH:20][CH:21]=1.[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:17]2[C:16]3[C:15](=[O:27])[N:14]4[C:28]([CH3:31])=[N:29][N:30]=[C:13]4[N:12]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:11]=3[N:10]=[C:9]2[N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 57600158HCID 57600158, compound

Product 2

HCID 66725524HCID 66725524, compoundYield 27%HCID 178446077HCID 178446077, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride 60% in mineral oil (18 mg, 0.74 mmol) was added to a solution of 1H-1,2,4-Triazole (45 mg, 0.65 mmol) in DMF (10 mL) at room temperature. After stirring for 1 hour at room temperature, 7-bromo-6-(4-methoxybenzyl)-3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (200 mg, 0.40 mmol) in DMF was added to above solution and the mixture was stirred overnight. The reaction was quenched with a drop of water and the reaction mixture was purified by pre LC-MS to give the desired product (53 mg, 27.2%) and its region-isomer 6-(4-methoxybenzyl)-3-methyl-9-pentyl-7-(1H-1,2,4-triazol-1-yl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (53 mg, 27%). LCMS calculated for C22H26N9O2(M+H): 448.2; found 448.2.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction was quenched with a drop of water
  3. customthe reaction mixture was purified by pre LC-MS

Sources & evidence

ORD record
ord-b664956537524458a430bb8caaff43a3
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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