Methyl iodide → HCID 68588479, compound

HRID 2070917Notes

Reaction equation

HRID 2070917 reaction equation
O1CCC(C2N=C3C=CC=C(N)N3N=2)[CH2:2]1.[Br:16][C:17]1[N:31]=[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([NH:25][C@@H:26]3[CH2:30][CH2:29][O:28][CH2:27]3)[N:19]2[N:18]=1.[H-].[Na+].IC>COCCOC.C(OCC)(=O)C>[Br:16][C:17]1[N:31]=[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([N:25]([CH3:2])[C@@H:26]3[CH2:30][CH2:29][O:28][CH2:27]3)[N:19]2[N:18]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68588791HCID 68588791, compoundHCID 86640822HCID 86640822, compound

Product 1

HCID 68588479HCID 68588479, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(R)-2-Bromo-N-methyl-N-(tetrahydrofuran-3-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine. (R)-2-Bromo-N-(tetrahydrofuran-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine (500.0 mg, 1.766 mmol) was suspended in 1,2-dimethoxyethane (8.83 mL) and cooled to 0° C. The reaction was purged with nitrogen followed by the addition of sodium hydride (89.0 mg, 3.53 mmol, 95%). The mixture was allowed to stir for 10 min. Iodomethane (330.0 μL, 5.30 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature and stir for 16 h. Ethyl acetate was added to the reaction and allowed to stir for 1 min followed by an extraction with ethyl acetate and water. The organics were washed with brine and dried with magnesium sulfate. Organic volatiles were removed under reduced pressure and purified using silica gel chromatography on an Emrys Biotage SP1 (10-100% ethyl acetate in hexanes) over 1.2 L. The desired fractions were combined and organic volatiles removed under reduced pressure to afford (R)-2-bromo-N-methyl-N-(tetrahydrofuran-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine (373.8 mg, 1.258 mmol, 71.2% yield). MS (ESI) m/z 297.1 [M]+, 299.1 [M+2]+.

Workup

  1. customThe reaction was purged with nitrogen
  2. temperatureto warm to room temperature
  3. stirringstir for 16 h
  4. stirringto stir for 1 min
  5. extractionfollowed by an extraction with ethyl acetate and water
  6. washThe organics were washed with brine
  7. dry with materialdried with magnesium sulfate
  8. customOrganic volatiles were removed under reduced pressure
  9. custompurified
  10. customorganic volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-9f8ceccda205412281d38e499db91c05
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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