Hydrochloric Acid → 5-bromo-7H-[1,2,4]triazolo[4,3-a]pyrazin-8-one

HRID 575704Notes

Reaction equation

HRID 575704 reaction equation
[Br:1][C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5]([O:11]C)=[N:4][CH:3]=1.Cl>CC(O)=O>[Br:1][C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5](=[O:11])[NH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 584469805-Bromo-8-methoxy-[1,2,4]triazolo[4,3-A]pyrazine

Product 1

HCID 1180214495-bromo-7H-[1,2,4]triazolo[4,3-a]pyrazin-8-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-8-methoxy-[1,2,4]triazolo[4,3-a]pyrazine (Borchardt WO2011/112766) (500 mg, 2.18 mmol) in HOAc (3 mL) was added HCl (1 N, 5.00 mL). The mixture was heated at 110° C. for 4 h and concentrated to give the title compound (400 mg, yield: 85%) as a yellow solid which was carried on without purification. 1H NMR (DMSO-d6, 400 MHz): δ 11.78 (s, 1H), 9.25 (s, 1H), 7.25 (d, J=6.0 Hz, 1H). LCMS: 214.9 (M+H)+

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-a7fdd160f627442aa2a17fb756cdf814
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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