2-Bromopropanedial → {6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}methanol

HRID 1453137Notes

Reaction equation

[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][OH:8])[N:3]=1.[Br:9][CH:10]([CH:13]=O)[CH:11]=O>C(O)(=O)C>[Br:9][C:10]1[CH:11]=[N:1][C:2]2[N:6]([N:5]=[C:4]([CH2:7][OH:8])[N:3]=2)[CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a slurry of (5-amino-1H-[1,2,4]triazol-3-yl)-methanol (6.29 g, 33.12 mmol) in acetic acid (25 ml) was added bromomalonaldehyde (5 g, 33.12 mmol). The mixture was heated at 60° C. for 5 hours, and then cooled to room temperature. The light yellow solid was formed. After the solid were removed by filtration followed by drying in vacuum oven provides the light yellow solid as desired product, the filtrate was concentrate by rotary evaporation to give yellow oil. The crude oil was purified by flash chromatography (2% MeOH in CH2Cl2) to give the desired product as light yellow solid (combine total 6.5 g, 86% yield). 1H NMR (300 MHz, DMSO-D6) δ ppm 4.65 (d, J=5.46 Hz, 2H) 5.50-5.67 (m, 1H) 8.94 (d, J=2.45 Hz, 1H) 9.83 (d, J=2.26 Hz, 1H). MS: (APCI) 230 (M+H)

Workup

temperaturecooled to room temperature
customThe light yellow solid was formed
customAfter the solid were removed by filtration
customby drying in vacuum oven

Sources & evidence

ORD record: ord-194d10d210844780bfdb9f782cb1898d
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473790B2

Reaction notes

Loading…