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

HRID 1438319Notes

Reaction equation

HRID 1438319 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][OH:8])[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:6]([N:5]=[C:4]([CH2:7][OH:8])[N:3]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 147646ChloromalonaldehydeHCID 178508559HCID 178508559, compound

Product 1

HCID 23056782(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a slurry of (5-amino-1H-[1,2,4]triazol-3-yl)-methanol (28.5 g, 150 mmol, from step 6 of example A(1)) 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, the product crystallized out as a white solid (25.5 g, 92%). 1H NMR (300 MHz, DMSO-d6): δ 4.67 (s, 2H), 5.62 (s, 1H), 8.94 (d, J=2.45 Hz, 1H), 9.81 (d, J=2.45 Hz, 1H).

Workup

  1. temperatureUpon cooling of the reaction
  2. customthe product crystallized out as a white solid (25.5 g, 92%)

Sources & evidence

ORD record
ord-d3f33cd180eb4daf9905eb3a1e4a1bf5
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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