2-Amino-3-methylpyridine → HCID 86619140, compound

HRID 2238651Notes

Reaction equation

HRID 2238651 reaction equation
BrN1C(=O)CCC1=O.[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[C:12](/[CH:27]=[CH:28]/OCC)[N:11]=1.O1CCOCC1.[NH2:38][C:39]1[C:44]([CH3:45])=[CH:43][CH:42]=[CH:41][N:40]=1>C(OCC)(=O)C.O>[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])=[C:12]([C:27]2[N:40]3[CH:41]=[CH:42][CH:43]=[C:44]([CH3:45])[C:39]3=[N:38][CH:28]=2)[N:11]=1

Participants

7

Reactant 4

HCID 153472-Amino-3-methylpyridineHCID 312751,4-DioxaneHCID 67184N-bromobutanimideHCID 86619139HCID 86619139, compound

Product 1

HCID 86619140HCID 86619140, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

200 mg of N-bromosuccinimide was added to the mixture of 400 mg of 2-chloro-6-[(E)-2-ethoxyvinyl]-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purine [56-2], 10 mL of 1,4-dioxane, and 2 mL of water under an ice-cold condition, and stirred at the same temperature for 30 minutes. Thereto, 122 mg of 2-amino-3-picoline was added, stirred at 50° C. for 1 hour, and the reaction mixture was cooled back to room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine in the subsequent order, and the thus obtained organic layer was dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to obtain 360 mg of 2-chloro-6-(8-methylimidazo[1,2-a]pyridin-3-yl)-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purine [56-3] as a light brown solid.

Workup

  1. stirringstirred at 50° C. for 1 hour
  2. washwashed with water and saturated brine in the subsequent order
  3. dry with materialthe thus obtained organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe insolubles were filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ae67683ccf0f43f08976b987e72bcbe7
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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