Methyl iodide → 7-(2-(Methylamino)phenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 64277Notes

Reaction equation

HRID 64277 reaction equation
[C:1]([C:3]1[C:4]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)=[N:5][N:6]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:18][C:19](=O)C(F)(F)F)=[CH:10][CH:9]=[N:8][C:7]=12)#[N:2].[OH-].[K+].CI>CC(C)=O>[CH3:19][NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[N:6]2[N:5]=[C:4]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)[C:3]([C:1]#[N:2])=[C:7]2[N:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 117668126HCID 117668126, compound

Product 1

HCID 1176680947-(2-(Methylamino)phenyl)-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-(2-(3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-2,2,2-trifluoroacetamide (50 mg, 0.1 mmol) in 5 mL of acetone was added KOH (11.2 mg, 0.2 mmol) and CH3I (0.5 mL). The reaction mixture was stirred at It for 15 hr, then concentrated to remove acetone. The residue was partitioned between 20 mL of water and 20 mL of EA. The organic layer was concentrated and purified by pre-TLC (PE/EA=2/1) to give the product as a white solid (15 mg, yield: 37%). 1H NMR (DMSO-d6) δ 8.82 (d, J=4.4 Hz, 1H), 7.97 (d, J=8.8 Hz, 2H), 7.47-7.38 (m, 4H), 7.31 (dd, J=1.6, 7.2 Hz, 1H), 7.23-7.17 (m, 3H), 7.11 (d, J=8.8 Hz, 2H), 6.77-6.69 (m, 2H), 5.35-5.31 (m, 1H), 2.68 (d, J=4.8 Hz, 3H). MS (ESI) m/e [M+1]+ 417.9.

Workup

  1. concentrationconcentrated
  2. customto remove acetone
  3. customThe residue was partitioned between 20 mL of water and 20 mL of EA
  4. concentrationThe organic layer was concentrated
  5. custompurified by pre-TLC (PE/EA=2/1)

Sources & evidence

ORD record
ord-4f80255465ed46a389c625d5d13a7540
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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