Water → HCID 89463674, compound

HRID 530029Notes

Reaction equation

HRID 530029 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]2[N:8]=[C:9]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[C:10]([C:11]#[N:12])=[C:4]2[NH:3]1.[H-].[Na+].[CH3:21]I.O>CN(C=O)C>[CH3:21][N:3]1[C:2](=[O:1])[CH2:7][CH2:6][N:5]2[N:8]=[C:9]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[C:10]([C:11]#[N:12])=[C:4]12

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136507783HCID 136507783, compound

Product 1

HCID 89463674HCID 89463674, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-oxo-2-(pyridin-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (50 mg, 0.21 mmol) in DMF (2 mL) was added NaH (17 mg, 0.42 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 mins, then methyl iodide (30 mg, 0.21 mmol) was added. The mixture was stirred at 0° C. for an additional 30 mins. 1 mL of water was added to quench the reaction which was extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated in vacuo. The residue was purified by HPLC to afford 4-methyl-5-oxo-2-(pyridine-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile: MS (m/z): 254.1 [M+H]+, 1H NMR (CD3OD, 400 MHz): δ8.06 (s, 1 H), 8.60 (d, 1 H, J=1.6 Hz), 8.36 (d, 1H, J=8.0 Hz), 7.59 (dd, 1 H, J=8.0 Hz, J=56 Hz), 4.44 (t, 2 H, J=7.6 Hz), 3.04 (t, 2H, J=7.6 Hz).

Workup

  1. stirringThe mixture was stirred at 0° C. for an additional 30 mins
  2. customto quench
  3. customthe reaction which
  4. extractionwas extracted with ethyl acetate
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-e285f087c39a4ca1b1f4731e06204f5b
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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