Isopropanol → HCID 59359758, compound

HRID 1187273Notes

Reaction equation

HRID 1187273 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][N:12]=[C:11]2Cl.CC(O)C>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][N:12]=[C:11]2[O:4][CH:2]([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 167703106-Bromo-4-chloro-quinazolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 59359758HCID 59359758, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Potassium t-butoxide (4.1 ml, 4.1 mmol; 1M in THF) was added to a suspension mixture of 6-bromo-4-chloro-quinazoline (1.0 g, 4.0 mmol) and 2-propanol (0.313 ml, 4.1 mmol) in THF (20 ml). After stirring at 50° C. for 30 minutes, the mixture was cooled to room temperature and the THF was removed in vacuo. The residue was taken up in ethyl acetate (50 ml) and the organic layer was washed with water followed by brine. The organic layer was dried over Na2SO4 and the residue purified by silica gel chromatography with gradient of 11 to 32% ethylacetate-hexane. Product containing fractions were pooled and concentrated to afford the title compound as beige solid (0.93 g, yield: 85%). The resulting compound was characterized as follows: MS (m/z) 266.75 [M+H]+; HPLC Rt=1.68 minutes (Method A).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. customthe THF was removed in vacuo
  3. washthe organic layer was washed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe residue purified by silica gel chromatography with gradient of 11 to 32% ethylacetate-hexane
  6. additionProduct containing fractions
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7c3be977ccc6483d864cb36de1b0bff8
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

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