Potassium Carbonate → HCID 59242065, compound

HRID 1876165Notes

Reaction equation

HRID 1876165 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:22][CH3:23])[CH:8]=2)[N:3]=1.Cl.[CH3:25][NH2:26].C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[CH3:23][O:22][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:26][CH3:25])[N:11]=[C:10]2[N:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 59242113HCID 59242113, compound

Product 1

HCID 59242065HCID 59242065, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2-chloro-6-methoxy-quinazoline-4-yl)-(4-methoxy-phenyl)-methyl-amine (0.15 g, 0.45 mmol), methylamine hydrochloride (0.3 g, 4.5 mmol), potassium carbonate (0.68 g, 4.4 mmol) in 4 mL of iPrOH in a sealed tube stirred at 90° C. overnight. The reaction mixture was concentrated under reduced pressure, the residue dissolved in chloroform 20 mL, washed with conc. Sodium bicarbonate, brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (CHCL3/MeOH/NH4OH=10/1/0.1 as eluent) yielding 45 mg (32%) of the title compound. 1H NMR (DMSO): δ 7.2 (d, 1H), 7.18-7.15 (m, 2H), 7.05-7.02 (d, 1H), 6.99-6.97 (d, 2H), 6.5 (br s, 1H), 6.2 (s, 1H), 3.7 (s, 3H), 3.4 (s, 3H), 3.2 (s, 3H), 2.8 (s, 3H). LC/MS: 325, (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in chloroform 20 mL
  3. washwashed with conc. Sodium bicarbonate, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by chromatography on silica gel (CHCL3/MeOH/NH4OH=10/1/0.1 as eluent)

Sources & evidence

ORD record
ord-659ea0ca2ec04a2dae9fc68bb52bc18e
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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