Sodium Methoxide → HCID 22046298, compound

HRID 1830766Notes

Reaction equation

HRID 1830766 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[O:10])=[N:6][CH:7]=1.[CH3:21][O-:22].[Na+]>CN1C(=O)CCC1.C(OCC)(=O)C>[CH3:20][O:19][C:13]1[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[NH:11][C:9]([NH:8][C:5]1[CH:4]=[N:3][C:2]([O:22][CH3:21])=[CH:7][N:6]=1)=[O:10]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 22046384HCID 22046384, compound

Product 1

HCID 22046298HCID 22046298, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 1-(5-bromo-pyrazin-2-yl)-3-(2-methoxy-5-methyl-phenyl)-urea (47 mg; 0.14 mmol) in N-methyl pyrrolidinone (300 μL) was added sodium methoxide (0.5 mmol). The reaction was heated to 100° C. After stirring for 12 hours, the reaction was cooled to room temperature, diluted with 30 mL of ethyl acetate and washed with aqueous 10% sodium carbonate (1×30 mL), brine (30 mL), then dried (MgSO4), and filtered. The crude product was purified using a 0.5 mm prep plate eluting with hexane and ethyl acetate (1:1) to yield a yellow solid (13% yield). 1H NMR (400 MHz, CDCl3) δ8.12 (s, 1H), 7.99 (s, 1H), 7.91 (s, 1H), 6.80 (dd, 2H), 3.95 (s, 3H), 3.89 (s, 3H), 2.38 (s, 3H). LRMS (ESI, Positive) m/e 289.10 (M+1).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. washwashed with aqueous 10% sodium carbonate (1×30 mL), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe crude product was purified
  6. washeluting with hexane and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-3b06ed3630434c56af7636094e32b20d
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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