1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(4-(5-iodo-2-methoxypyrimidin-4-yloxy)phenyl)-5-methylpyridin-2-amine

HRID 473738Notes

Reaction equation

HRID 473738 reaction equation
[I:1][C:2]1[C:3](=[O:10])[N:4]=[C:5]([O:8][CH3:9])[NH:6][CH:7]=1.N12CCCN=C1CCCCC2.[CH3:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]2[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=2)=[N:27][CH:28]=1>C(#N)C.CCOC(C)=O>[I:1][C:2]1[C:3]([O:10][C:33]2[CH:32]=[CH:31][C:30]([NH:29][C:26]3[CH:25]=[CH:24][C:23]([CH3:22])=[CH:28][N:27]=3)=[CH:35][CH:34]=2)=[N:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 593739864-(5-Methylpyridin-2-ylamino)phenolHCID 178494260HCID 178494260, compound

Product 1

HCID 59374006N-(4-(5-iodo-2-methoxypyrimidin-4-yloxy)phenyl)-5-methylpyridin-2-amine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 5-iodo-2-methoxypyrimidin-4(1H)-one (0.12 g, 0.46 mmol) and (1H-benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate(V) (0.24 g, 0.55 mmol) in acetonitrile (4 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.14 mL, 0.91 mmol). The reaction mixture was stirred at room temperature for 30 min before 4-(5-methylpyridin-2-ylamino)phenol (0.27 g, 1.37 mmol) was added. The reaction mixture was stirred at room temperature for an additional 1 h. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was separated, washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography to give N-(4-(5-iodo-2-methoxypyrimidin-4-yloxy)phenyl)-5-methylpyridin-2-amine. MS (ESI, pos. ion) m/z: 435.1 (M+1).

Workup

  1. additionwas added
  2. washwashed with water
  3. customThe organic layer was separated
  4. washwashed with sat. sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6c070034c13c459484b4a55730bfb41c
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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