Sodium ethoxide → HCID 44193082, compound

HRID 1855377Notes

Reaction equation

HRID 1855377 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]3)=[C:12]([O:22][CH3:23])[CH:11]=2)[N:3]=1.[O-:24][CH2:25][CH3:26].[Na+]>C(O)C>[CH2:25]([O:24][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]3)=[C:12]([O:22][CH3:23])[CH:11]=2)[N:3]=1)[CH3:26]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 57829826HCID 57829826, compound

Product 1

HCID 44193082HCID 44193082, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (4-chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (165 mg, 0.5 mmol) and sodium ethoxide (54 mg, 0.75 mmol) in ethanol (3 ml) was heated for 30 min to 160° C. in a microwave oven. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was stirred with diethyl ether for 30 min to yield the title compound as a brown solid (139 mg, 82%).

Workup

  1. temperaturewas heated for 30 min to 160° C. in a microwave oven
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f44f794585734c09b3c70e850dafccd2
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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