Sodium Methoxide → HCID 44193085, compound

HRID 1855414Notes

Reaction equation

HRID 1855414 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.[CH3:24][O-:25].[Na+]>CO>[CH3:23][O:22][C:12]1[CH:11]=[C:10]([NH:9][C:4]2[N:3]=[C:2]([O:25][CH3:24])[CH:7]=[C:6]([CH3:8])[N:5]=2)[CH:15]=[CH:14][C:13]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57829826HCID 57829826, compound

Product 1

HCID 44193085HCID 44193085, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (4-chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (99 mg, 0.3 mmol) and sodium methoxide (25 mg, 0.45 mmol) in methanol (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 aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by reversed preparative HPLC using acetonitril/water (0.1% formic acid) to yield the title compound as a yellow solid (30 mg, 31%). MS ISP (m/e): 326.2 (100) [(M+H)+].

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. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by reversed preparative HPLC

Sources & evidence

ORD record
ord-699130e53a3e4143aed47a78201b7ae2
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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