Methyl iodide → HCID 117668117, compound

HRID 64297Notes

Reaction equation

HRID 64297 reaction equation
[C:1]([C:3]1[C:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)=[N:5][N:6]2[C:11]([CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=[N:8][C:7]=12)#[N:2].[C:33]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[C:1]([C:3]1[C:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)=[N:5][N:6]2[C:11]([CH2:12][N:13]([CH3:33])[C:14](=[O:19])[C:15]([F:16])([F:17])[F:18])=[CH:10][CH:9]=[N:8][C:7]=12)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 117668011HCID 117668011, compound

Product 1

HCID 117668117HCID 117668117, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of N-((3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)methyl)-2,2,2-trifluoroacetamide (40 mg, 0.091 mmol) in 5 mL of acetone was added K2CO3 (50 mg) and CH3I (0.5 mL). After stirring at rt for 4 hr, the mixture was concentrated. The residue was partitioned between 10 mL of water and 10 mL of DCM. The organic layer was concentrated and purified by Pre-TLC (DCM/MeOH=20/1) to give a yellow solid (30 mg, 73%). MS (ESI) m/e [M+1]+ 451.9.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between 10 mL of water and 10 mL of DCM
  3. concentrationThe organic layer was concentrated
  4. custompurified by Pre-TLC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-f4b2a19eb4814ce4b5053ffd359b3305
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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