Hydrazinecarboxaldehyde → 9-bromopyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 926111

Reaction equation

HRID 926111 reaction equation
[CH:1]([NH:3][NH2:4])=[O:2].[Br:5][C:6]1[CH:7]=[C:8]([C:17]#[N:18])[C:9]([NH:12]C(=O)OC)=[N:10][CH:11]=1.[CH3:19]N1CCCC1=O>>[Br:5][C:6]1[CH:11]=[N:10][C:9]2[NH:12][C:1](=[O:2])[N:3]3[N:4]=[CH:19][N:18]=[C:17]3[C:8]=2[CH:7]=1

Participants

4

Reactant 3

HCID 12229HydrazinecarboxaldehydeHCID 13387N-methyl-2-pyrrolidoneHCID 86705383Methyl 5-bromo-3-cyanopyridin-2-ylcarbamate

Product 1

HCID 1363380329-bromopyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-oneYield 60%

Conditions

Temperature
120 °C

Procedure

Formyl hydrazine (60 mg, 1.0 mmol) was added to a solution of methyl 5-bromo-3-cyanopyridin-2-ylcarbamate (255 mg, 1.0 mmol) in 1-methylpyrrolidinone (5 mL). The resulting mixture was stirred at 120° C. for 3 h. The mixture was cooled to room temperature and poured into ice-water (20 mL). The resulting solid was separated by filtration, washed with water and hexanes and dried under vacuum to afford the title compound (160 mg, 60%). 1H NMR (400 MHz, DMSO-d6) δ 8.60 (s, 1H), 8.70 (s, 1H), 8.80 (s, 1H), 13.00 (br s, 1H). [M+H]=266.3.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe resulting solid was separated by filtration
  3. washwashed with water and hexanes
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b655ac79572347d6adb6b7d29dc6112e
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Linked notes

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