Dichloromethane → HCID 86631989, compound

HRID 2361075Notes

Reaction equation

HRID 2361075 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[N:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl[C:16]1[C:21]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH3:29])[N:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1.C(Cl)Cl>O>[Br:7][C:8]1[N:13]=[CH:12][C:11]([O:14][C:16]2[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH3:29])[N:23]=3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27628652-Bromo-5-hydroxypyridineHCID 161090044-(2-chloro-3-pyridinyl)-N-methyl-2-pyrimidinamine

Product 1

HCID 86631989HCID 86631989, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

To a slurry of cesium carbonate (8.9 g, 27 mmol) and 6-bromopyridin-3-ol (2.6 g, 15 mmol) was added 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine (3.0 g, 14 mmol). The reaction mixture was sealed and heated to 125° C. for 16 h. The mixture was cooled and diluted with water and the aqueous solution was extracted with DCM (3×75 mL). The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a brown oil, which was taken up in a little DCM and purified on an ISCO 120 g column, eluting with a gradient of 0-100% EtOAc/DCM, to afford 4-(2-(6-bromopyridin-3-yloxy)pyridin-3-yl)-N-methylpyrimidin-2-amine as an off-white solid. MS m/z=295 [M+H]+. Calc'd for C15H12BrN5O: 358.2.

Workup

  1. customThe reaction mixture was sealed
  2. temperatureThe mixture was cooled
  3. extractionthe aqueous solution was extracted with DCM (3×75 mL)
  4. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil, which
  8. custompurified on an ISCO 120 g column
  9. washeluting with a gradient of 0-100% EtOAc/DCM

Sources & evidence

ORD record
ord-45694051b6254ce28855bd98b151af18
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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