Ammonium Chloride → HCID 10334841, compound

HRID 1609853Notes

Reaction equation

HRID 1609853 reaction equation
Cl[C:2]1[C:3]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.[CH3:22][O-:23].[Na+].[NH4+].[Cl-]>C1COCC1>[CH3:22][O:23][C:2]1[C:3]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 103575922-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 10334841HCID 10334841, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine (30 mg, 0.094 mmol) in THF (5 mL) is added sodium methoxide (25% w/w in methanol, 0.5 mL). The mixture is refluxed for 1 hour. On cooling, saturated NH4Cl (0.7 mL) is added to quenched the reaction. Solvent is removed in vacuo and to the residue is added DCM (30 mL). The mixture is then dried and solvent removed to give 21 mg of 2-[1-(3,5-dimethoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine as an oil. 1H NMR (CDCl3) 8.79 (d, 2H), 7.62 (s, 1H), 7.15–7.21 (m, 2H, 7.07 (s, 1H), 5.95 (s, 2H), 3.88 (s, 3H), 3.82 (s, 3H) I. 2-[1-(5-Methoxy-3-piperidin-1-yl-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine (Compound 10)

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. temperatureOn cooling
  3. customto quenched
  4. customthe reaction
  5. customSolvent is removed in vacuo and to the residue
  6. additionis added DCM (30 mL)
  7. customThe mixture is then dried
  8. customsolvent removed

Sources & evidence

ORD record
ord-ff435f1554904e678cc24020dd0196d5
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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