2-Acetylcyclopentanone → (8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-methanol

HRID 638877

Reaction equation

HRID 638877 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][CH2:6][C:5]1=O)(=O)[CH3:2].[NH2:10][C:11]1[NH:15][N:14]=[C:13]([CH2:16][OH:17])[N:12]=1>COCCO>[CH3:2][C:1]1[N:15]2[N:14]=[C:13]([CH2:16][OH:17])[N:12]=[C:11]2[N:10]=[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=12

Participants

4

Reactant 2

HCID 984712-AcetylcyclopentanoneHCID 178508559HCID 178508559, compound

Product 1

HCID 68701675(8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-methanolYield 32.7%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a round bottomed flask was loaded 3.78 grams of 2-acetylcyclopentanone, 3.52 grams of (5-Amino-1H-[1,2,4]triazol-3-yl)-methanol and 50 ml 2-methoxyethanol. The mixture was refluxed for 18 hours. Then it was cooled down to 23° C. and concentrated to 5 ml. Then 50 ml ethyl ether was added and the precipitate was filtered and vacuum dried to yielded 2.0 grams of product. This compound was used directly for the next step. MS: 205.2 (M+H). H-NMR (DMSO): δ 5.55 (t, 1H, OH, J=6.2 Hz), 4.63 (d, 2H, J=6.2 Hz), 3.28 (m, 2H), 3.02 (t, 2H, CH2, J=6.8 Hz), 2.51 (s, 3H, CH3), 2.27 (m, 2H, CH2).

Workup

  1. customTo a round bottomed flask was loaded
  2. temperatureThe mixture was refluxed for 18 hours
  3. concentrationconcentrated to 5 ml
  4. additionThen 50 ml ethyl ether was added
  5. filtrationthe precipitate was filtered
  6. customvacuum dried

Sources & evidence

ORD record
ord-9f2bf200b4fc4cc288e0c4f002cf94ac
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Linked notes

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