Water → 5-Bromo-7-methyl-[1,2,4]triazolo[4,3-a]pyrazin-8-one

HRID 575705Notes

Reaction equation

[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.[H-].[Na+].[CH3:14]I.O>CN(C=O)C.C(Cl)Cl.CC(O)C>[Br:1][C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5](=[O:11])[N:4]([CH3:14])[CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of the title compound of step 1 (400 mg, 1.86 mmol) in DMF (4 mL) was added NaH (149 mg, 3.72 mmol, 60% in mineral oil) in portions at 0° C. under N2. The mixture was stirred at 20° C. for 1 h, and methyl iodide (792 mg, 5.58 mmol) was added. After stirring at 20° C. for 5 h, water was added. Methylene chloride:2-propanol (10:1) extractive work up gave the title compound (200 mg, yield: 47%) as a light yellow solid which was carried on without purification. 1H NMR (DMSO-d6, 400 MHz): δ 9.26 (s, 1H), 7.60 (s, 1H), 3.42 (s, 3H). LCMS: 228.9 (M+H)+

Workup

stirringAfter stirring at 20° C. for 5 h

Sources & evidence

ORD record: ord-909bd0fb458f4f5c9184da773761351d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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