Chloromalonaldehyde → (6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

HRID 858698Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a slurry of (3-amino-1H-1,2,4-triazol-5-yl)methanol (28.5 g, 150 mmol) in acetic acid was added chloromalonaldehyde (16 g, 150 mmol). The mixture was heated to 80° C. for 4 hours. Upon cooling of the reaction to room temperature, the product crystallized out as a white solid (25.5 g, 92%). 1H NMR (300 MHz, DMSO-D6) δ: 4.67 (s, 2 H), 5.62 (s, 1 H), 8.94 (d, J=2.45 Hz, 1 H), 9.81 (d, J=2.45 Hz, 1 H). MS (APCI): 185.0 (M+H+).

Workup

temperatureUpon cooling of the reaction to room temperature
customthe product crystallized out as a white solid (25.5 g, 92%)

Sources & evidence

ORD record: ord-5634630aa557414caebbf49178a87f7b
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Reaction notes

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