Water → HCID 86698303, compound

HRID 2408990Notes

Reaction equation

HRID 2408990 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([CH3:16])[N:3]=1.[NH2:17][C:18]1[CH:19]=[C:20]([C:24]([O-:26])=[O:25])[Se:21][C:22]=1[CH3:23].O.[CH:28](O)(C)C>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[C:4]([CH3:16])[N:3]=[C:2]2[NH:17][C:18]1[CH:19]=[C:20]([C:24]([O:26][CH3:28])=[O:25])[Se:21][C:22]=1[CH3:23]

Participants

5

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 104901504-Chloro-6,7-dimethoxy-2-methylquinazolineHCID 86698304HCID 86698304, compound

Product 1

HCID 86698303HCID 86698303, compoundYield 57%

Procedure

To a solution of 4-chloro-6,7-dimethoxy-2-methylquinazoline (From example 24; 700 mg, 2.93 mmol) in isopropanol (20 mL) was added 4-amino-5-methylselenophene-2-carboxylate (1.3 g, 5.8 mmol) at rt and the mixture was stirred at rt for 16 h. The mixture was poured into ice cooled water and stirred for 10 min. The solution was extracted with EtOAc (3×100 mL) and the combined layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (98:2) as eluents to give the product (700 mg, 57%) as a brown color solid, mp 200-204° C. 1H NMR (400 MHz, CDCl3): δ 8.18 (1H, s), 7.19 (1H, s), 7.00 (1H, s), 3.98 (3H, s), 3.92 (3H, s), 3.85 (3H, s), 2.58 (3H, s), 2.46 (3H, s); 13C NMR (100 MHz, CDCl3): δ 163.5, 162.8, 156.9, 154.8, 148.7, 148.2, 144.0, 135.3, 135.1, 131.8, 107.3, 106.4, 99.8, 56.2, 56.1, 52.2, 26.2, 15.5; LC-MS (positive ion mode): m/z 420, 422 (M+H)+.

Workup

  1. additionThe mixture was poured into ice
  2. stirringstirred for 10 min
  3. extractionThe solution was extracted with EtOAc (3×100 mL)
  4. washthe combined layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. customevaporated the solvent
  8. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-ae3f5be0c4dc46bead14dee35c79e395
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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