tert-Butyl 4-(5-(hydroxymethyl)-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate → Tert-butyl 4-(5-formyl-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate

HRID 1045716Notes

Reaction equation

HRID 1045716 reaction equation
[OH:1][CH2:2][C:3]1[N:8]2[CH:9]=[N:10][N:11]=[C:7]2[C:6]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:5][CH:4]=1>O=[Mn]=O.C(Cl)Cl>[CH:2]([C:3]1[N:8]2[CH:9]=[N:10][N:11]=[C:7]2[C:6]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 58447010tert-Butyl 4-(5-(hydroxymethyl)-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate

Product 1

HCID 58447024Tert-butyl 4-(5-formyl-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A 250 mL round bottom flask was charged with tert-butyl 4-(5-(hydroxymethyl)-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate (0.30 g, 0.90 mmol) and dry CH2Cl2 (20 mL). To the above was added activated MnO2 (0.23 g, 2.6 mmol). The resulting suspension was stirred at room temperature for 16 h. Work-up: the reaction mixture was filtered. The filtrate was concentrated in vacuo, to afford 0.26 g (87%) of the product as a yellow solid. MS m/z: 333 (M+H+).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-53c5c913bcc4438598ef95ff14f7657c
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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