Methyl iodide → HCID 10236275, compound

HRID 1179125Notes

Reaction equation

HRID 1179125 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]4[C:19]=3[CH:18]=[CH:17][CH:16]=[N:15]4)[CH:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[CH:1]1([N:4]([CH3:22])[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]4[C:19]=3[CH:18]=[CH:17][CH:16]=[N:15]4)[CH:8]=[CH:7][N:6]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6918710N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine

Product 1

HCID 10236275HCID 10236275, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-yl-2-pyrimidinamine (25 mg, 0.1 mmol) in DMF (2 mL) was added sodium hydride (6 mg, 0.25 mmol) and methyl iodide (0.013 mL, 0.15 mmol). The reaction was allowed to stir for about 1 hour. The reaction was concentrated in vacuo. Water (10 mL) was added and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were dried (MgSO4) filtered and concentrated in vacuo. The residue was triturated with diethylether to give the title compound as light orange solid (20 mg, 80%). 1H-NMR (400 MHz, CDCl3) δ 9.07 (d, 1H, J=8.8 Hz), 8.46 (s, 1H), 8.35 (m, 2H) 7.12 (dd, 1H, J=8.8, 4.4 Hz), 6.89 (d, 1H, J=5.6 Hz), 3.23 (s, 3H), 2.85 (m, 1H), 0.94 (m, 2H), 0.73 (m, 2H); MS (ESI) (M+H)+ 267.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionWater (10 mL) was added
  3. extractionthe aqueous layer was extracted with EtOAc (2×30 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethylether

Sources & evidence

ORD record
ord-35dee585bb2c4882a4fecef04c93cc1f
Source dataset
uspto-grants-2007_10
Patent number
US07279473B2

Reaction notes

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