Triethylamine → HCID 69433538, compound

HRID 1890663Notes

Reaction equation

HRID 1890663 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([C:14]1[N:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:35]([C:37]1[NH:38][C:39]2[C:40]([N:47]=1)=[N:41][C:42]([CH3:46])=[CH:43][C:44]=2[CH3:45])[CH3:36].O.[OH-].[Li+]>ClCCl.C(Cl)(Cl)Cl.C(OCC)(=O)C.CO>[C:1]([O:5][C:6](=[O:22])[N:7]([C:14]1[N:19]=[CH:18][C:17]([CH2:20][N:47]2[C:40]3=[N:41][C:42]([CH3:46])=[CH:43][C:44]([CH3:45])=[C:39]3[N:38]=[C:37]2[CH2:35][CH3:36])=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 69434160HCID 69434160, compound

Product 1

HCID 69433538HCID 69433538, compoundYield 94.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(5-Hydroxymethylpyrimidin-2-yl)phenylcarbamic acid tert-butyl ester (286 mg, 0.949 mmol) obtained in Step 6 was dissolved in dichloromethane (10 mL), and triethylamine (0.265 mL, 1.90 mmol) and methanesulfonyl chloride (0.147 mL, 1.90 mmol) were added to the solution at 0° C., followed by stirring at room temperature for 2 hours. After the reaction was finished, the reaction mixture was added with methanol to decompose excess reagents, and the mixture was diluted with chloroform and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then the residue was dissolved in DMF (10 mL), and the solution was added with 2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine (234 mg, 1.34 mmol) and lithium hydroxide monohydrate (56.0 mg, 1.34 mmol) followed by stirring at 60° C. for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:1) to obtain [5-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)pyrimidin-2-yl]phenylcarbamic acid tert-butyl ester (412 mg, 81%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThen the residue was dissolved in DMF (10 mL)
  5. stirringby stirring at 60° C. for 3 hours
  6. washwashed with water and saturated brine
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-b958364658784ecf898dccc67f7580ae
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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