1-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-3-(methoxymethoxy)benzene → 3-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}phenol

HRID 1271283Notes

Reaction equation

HRID 1271283 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28]COC)[CH:23]=3)[CH3:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CO>CO>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([N:19]([CH2:21][C:22]3[CH:23]=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=3)[CH3:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 184526351-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-3-(methoxymethoxy)benzeneHCID 21893726Hydrochloride methanol2×

Product 1

HCID 184526533-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}phenolYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 0.91 g of 1-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-3-(methoxymethoxy)benzene in 10 ml of methanol, 2 ml of a 18% hydrogen chloride-methanol solution was added. After stirring at room temperature for 2 hours, 1 ml of a 18% hydrogen chloride-methanol solution was further added and the mixture was continuously stirred for one hour. After the solvent was evaporated under reduced pressure, the reaction solution was neutralized by adding an aqueous saturated sodium hydrogen carbonate solution and then extracted with ethyl acetate. The crude crystal was washed with diethyl ether and then dried to obtain 0.66 g of the desired compound as a colorless crystal having a melting point of 156 to 157° C.

Workup

  1. additionwas added
  2. stirringthe mixture was continuously stirred for one hour
  3. customAfter the solvent was evaporated under reduced pressure
  4. additionby adding an aqueous saturated sodium hydrogen carbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe crude crystal was washed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-eae735c6b94f4327aa4c2d6bfc8f2ce6
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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