Methyl iodide → HCID 89463478, compound

HRID 530026Notes

Reaction equation

HRID 530026 reaction equation
[CH3:1][C:2]1[C:3]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:4][N:5]2[CH2:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=12.[H-].[Na+].I[CH3:21]>CN(C=O)C>[CH3:1][C:2]1[C:3]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:4][N:5]2[CH2:10][CH2:9][C:8](=[O:11])[N:7]([CH3:21])[C:6]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136507784HCID 136507784, compound

Product 1

HCID 89463478HCID 89463478, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methyl-2-(pyridine-3-yl)-6,7-dihydropyrazolo[1,5-a]pyrimidin-5(4H)-one (50 mg, 0.22 mmol) in DMF (5 mL) was added NaH (13 mg, 0.33 mmol). The resulting mixture was stirred at room temperature for 30 minutes, and then iodomethane (47 mg, 0.33 mmol) was added and stirred at room temperature for 30 minutes. The mixture was quenched with water (20 mL) and extracted with ethyl acetate (10 mL×2). The combined organic layers were dried, filtered, concentrated in vacuo and re-crystallized from MeOH to give 3,4-dimethyl-2-(pyridine-3-yl)-6,7-dihydropyrazolo[1,5-a]pyrimidin-5(4 H)-one: MS (m/z): 243.1 [M+H]+, 1HNMR (400 MHz, CD3OD) δ 8.74 (s, 1H), 8.55 (d, 1 H, J=4.0 Hz), 8.03 (d, 1 H, J=8.0 Hz), 7.54 (dd, 1 H, J=4.8 Hz, J=8.0 Hz), 4.35 (t, 2H, J=6.8 Hz), 3.50 (s, 3 H), 2.95 (t, 2 H, J=6.8 Hz), 2.30 (s, 3H).

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. customThe mixture was quenched with water (20 mL)
  3. extractionextracted with ethyl acetate (10 mL×2)
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customre-crystallized from MeOH

Sources & evidence

ORD record
ord-53d129101d6048a2afe2f98db6db6e16
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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