Methyl iodide → HCID 9925415, compound

HRID 1067269Notes

Reaction equation

HRID 1067269 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:17])=[CH:8][C:9]=2[NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][OH:14])[N:4]([C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:3]=1.[H-].[Na+].[CH3:29]I>O1CCCC1>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:17])=[CH:8][C:9]=2[NH:11][CH:12]([CH2:13][O:14][CH3:29])[CH2:15][CH3:16])[N:4]([C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21192903HCID 21192903, compound

Product 1

HCID 9925415HCID 9925415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[3,6dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridin-4-ylamino]-butan-1-ol (69 mg, 0.196 mmol) in 1 ml of dry tetrahydrofuran was treated with 60% sodium hydride oil (28 mg, 0.7 mmol). After stirring for 3 minutes, methyliodide (0.3 ml) was added and the mixture was stirred at room temperature for 1.5 hours. The mixture was quenched with water and extracted with ether. The organic layer was washed with water, dried and concentrated to give 61 mg of crude material. The residue was purified through silica gel column chromatography using chloroform as eluent to give 43 mg of the title compound in yellow glass form. 1H NMR (CDCl3): 6.91 (s, 2H), 6.00 (s, 1H), 5.05 (d, 1H), 3.4-3.6 (m, 2h), 3.41 (s, 3H), 2.66 (s, 3H), 2.28 (s, 3H), 1.92 (s, 3H), 1.91 (s, 3H), 1.6-1.8 (m, 2H), 1.05 (t, 3H), ppm; IR (CHCl3) 2920, 1586 cm−1; High MS calc. 366.2413, found 3.66.24516. The glass form was converted to the corresponding HCl salt form as a yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with ether
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customto give 61 mg of crude material
  8. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-6b1e6a2f37024f60bc4122fc113a6049
Source dataset
uspto-grants-2001_06
Patent number
US06248753B1

Reaction notes

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