Methyl iodide → HCID 86677075, compound

HRID 1520350Notes

Reaction equation

HRID 1520350 reaction equation
[Cl:1][C:2]1[C:3]2[CH:16]=[CH:15][NH:14][C:4]=2[N:5]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1.[C:17]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C>[Cl:1][C:2]1[C:3]2[CH:16]=[CH:15][N:14]([CH3:17])[C:4]=2[N:5]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86677076HCID 86677076, compound

Product 1

HCID 86677075HCID 86677075, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-2-(pyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine (80 mg, 0.34 mmol, 1.0 eq.) in dry DMF (20 mL) was added Cs2CO3 (221 mg, 0.68 mmol, 2.0 eq.) and iodomethane (54.3 mg, 0.38 mmol, 1.1 eq.) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2.5 h. The reaction mixture was poured into ice water and extracted with EtOAc (20 mL×3). The combined organic layers were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 8:1) to give 65 mg of xlvi-a as brown solid (56.7%).

Workup

  1. extractionextracted with EtOAc (20 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 8:1)

Sources & evidence

ORD record
ord-6b82481c8c344b4c8a7625ea15380509
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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