Methyl iodide → HCID 58882929, compound

HRID 445714Notes

Reaction equation

HRID 445714 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([CH3:8])=[N:6][CH:7]=1.[CH3:10][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH3:10])[C:5]([CH3:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 3280088Npc3163472×HCID 219640965-Bromo-2-methylpyridin-3-amine

Product 1

HCID 58882929HCID 58882929, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-2-methyl-pyridin-3-ylamine (Stage 75.1.4, 3.81 mmol) in THF (25 ml) cooled with an ice-bath was added 1 M bis(trimethylsilyl)amide in THF (4.38 mmol). The RM was stirred for 1 h at rt then was added iodomethane (4.38 mmol). The RM was stirred for 1 h at rt. The RM was cooled with an ice-bath and was added 1 M bis(trimethylsilyl)amide in THF (1.9 mmol). The RM was stirred for 30 min at it then was added iodomethane (1.9 mmol). The RM was stirred for 1 h at it then was diluted with EtOAc and washed with aqueous Na2CO3, with brine, dried over Na2SO4, filtered and evaporated. The residue was taken in MeOH and separated by preparative HPLC. The first eluting pure fractions containing product were basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined fractions were washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a brown oil (HPLC: tR 1.88 min (Method A); M+H=201, 203 MS-ES). The second eluting pure fractions, that contained (5-bromo-2-methyl-pyridin-3-yl)-dimethyl-amine side product, were basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined fractions were washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a brown oil (HPLC: tR 2.01 min (Method A); M+H=215, 217 MS-ES).

Workup

  1. stirringThe RM was stirred for 1 h at rt
  2. temperatureThe RM was cooled with an ice-bath
  3. stirringThe RM was stirred for 30 min at it
  4. stirringThe RM was stirred for 1 h at it
  5. washwashed with aqueous Na2CO3, with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customseparated by preparative HPLC
  10. additionThe first eluting pure fractions containing product
  11. concentrationconcentrated
  12. extractionextracted with dichloromethane (2×)
  13. washThe combined fractions were washed with brine
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. customevaporated

Sources & evidence

ORD record
ord-a4be019cf1264b2bb7e8007693a92412
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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