Dimethylamine → HCID 59242096, compound

HRID 1876164Notes

Reaction equation

HRID 1876164 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.[CH3:24][NH:25][CH3:26].CO>>[CH3:23][O:22][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:25]([CH3:26])[CH3:24])[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

4

Reactant 3

HCID 674DimethylamineHCID 887MethanolHCID 59242113HCID 59242113, compound

Product 1

HCID 59242096HCID 59242096, compoundYield 75%

Conditions

Temperature
75 °C

Procedure

A mixture of (2-chloro-6-methoxy-quinazoline-4-yl)-(4-methoxy-phenyl)-methyl-amine (0.12 g, 0.36 mmol), 2.0M dimethylamine in methanol (1.44 mL, 2.91 mmol) in sealed tube was stirred at 70-80° C. overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with sodium bicarbonate, brine, dried over anhydrous MgSO4, filtered and concentrated to give 90 mg of the titled compound (75% yield). 1H NMR (DMSO): δ 7.28 (d, 1H), 7.20-7.18 (dd, 2H), 7.06-7.00 (d, 1H), 7.00-6.98 (dd, 2H), 6.2 (d, 1H), 3.7(s, 3H), 3.4 (s, 3H), 3.22 (s, 3H), 3.18 (s, 6H). LC\MS: 339, (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with sodium bicarbonate, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-908223ef64774b2fbc48501d93eb2412
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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