m-Chloroperbenzoic acid → 9-(1-hydroxy-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 926124

Reaction equation

HRID 926124 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH:18]4[CH2:20][O:19]4)=[CH:17][C:12]=3[C:11]3=[N:21][CH:22]=[N:23][N:10]3[C:9]2=[O:24])=[CH:5][CH:4]=1.ClC1C=CC=[C:30]([C:34]([O:36]O)=O)C=1.COC1C=C[C:43]([CH2:44][N:45]2C3N=CC(C=C)=CC=3C3=NC=NN3C2=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:19][CH:18]([C:16]1[CH:15]=[N:14][C:13]2[N:8]([CH2:7][C:6]3[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:9](=[O:24])[N:10]3[N:23]=[CH:22][N:21]=[C:11]3[C:12]=2[CH:17]=1)[CH2:20][N:45]1[CH2:30][CH2:34][O:36][CH2:43][CH2:44]1

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 867053866-(4-methoxybenzyl)-9-vinylpyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-oneHCID 1181150326-(4-Methoxybenzyl)-9-(oxiran-2-yl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

Product 1

HCID 727063249-(1-hydroxy-2-morpholinoethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-(4-Methoxybenzyl)-9-(oxiran-2-yl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one. 3-Chloroperbenzoic acid (139 mg, 0.62 mmol) was added to a stirred solution of 6-(4-methoxybenzyl)-9-vinylpyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 30, 138 mg, 0.41 mmol) in DCM (1.3 mL) and the mixture was stirred for 18 h. Saturated sodium bicarbonate (3 mL) was added to the reaction mixture and the mixture was stirred for 2 h. The reaction mixture was diluted with DCM (5 mL), and the organic layer was separated, dried (MgSO4), and concentrated under vacuum to afford the title compound (118 mg, 82%) as a yellow semi-solid, which was used without further purification in the next step.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-42d1fde8c5de4b68acb5a1cece9d55a0
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Linked notes

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