(5-amino-1H-1,2,4-triazol-3-yl)methanol → (6-Methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

HRID 1453076

Reaction equation

HRID 1453076 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([CH2:7][OH:8])[NH:4][N:3]=1.CCO/[CH:12]=[C:13](/[CH:15]=O)\[CH3:14]>C(O)(=O)C>[CH3:15][C:13]1[CH:12]=[N:1][C:2]2[N:3]([N:4]=[C:5]([CH2:7][OH:8])[N:6]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 222697(5-amino-1H-1,2,4-triazol-3-yl)methanolHCID 30848683-Ethoxy-2-methylacrylaldehyde

Product 1

HCID 58762279(6-Methyl-[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 solution of (3-amino-1H-1,2,4-triazol-5-yl)methanol (16.6 g, 87.6 mmol) in acetic cid was added 3-ethoxymethacrolein (10.0 g, 87.6 mmol), and the mixture was heated to 80° C. for 4 hours. Upon cooling of the reaction, the product crystallized out of solution. The collected product was a white solid (14.0 g, 92%). 1H NMR (300 MHz, DMSO-D6) δ: 2.38 (m, 3H) 4.63 (m, 2H) 5.52 (m, 1H) 8.75 (m, 1H) 9.21 (m, 1H). MS (APCI, M+H+): 163.1, 165.1.

Workup

  1. temperatureUpon cooling of the reaction
  2. customthe product crystallized out of solution

Sources & evidence

ORD record
ord-983d21440a264bcb9d636e9609093182
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Linked notes

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