Aniline → 8-cyclopentyl-7-methoxy-N-phenylquinazolin-2-amine

HRID 1609805Notes

Reaction equation

HRID 1609805 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([CH:14]([CH3:16])[CH3:15])[C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[N:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24](#N)[CH3:25]>>[CH:14]1([C:5]2[C:6]([O:12][CH3:13])=[CH:7][CH:8]=[C:9]3[C:4]=2[N:3]=[C:2]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:11]=[CH:10]3)[CH2:16][CH2:25][CH2:24][CH2:15]1

Participants

4

Reactant 3

HCID 6115AnilineHCID 6342AcetonitrileHCID 222602072-Chloro-8-isopropyl-7-methoxyquinazoline

Product 1

HCID 53303138-cyclopentyl-7-methoxy-N-phenylquinazolin-2-amineYield 37%

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloro-7-methoxy-8-(2-propyl)quinazoline (200 mg, 0.76 mmol) and aniline (212 mg, 2.28 mmol) in acetonitrile (3 mL) was heated at 90° C. for 60 hours in a sealed tube. The solvent was removed under reduced pressure, to the residue 5% sodium carbonate solution was added. The product was extracted with ethyl acetate (3×40 mL). The combined organic extract was washed with brine, dried (Na2SO4), and concentrated. The product was purified on a column of silica gel to give the title compound as a yellow solid (90 mg, 37%), mp 187–188° C.; 1H NMR (CDCl3) δ: 1.72–2.30 (complex, 8H, 4×CH2), 3.96 (s, 3H, OCH3), 4.33 (m, 1H, CH), 7.23–7.41 (m, 2H, Ar-H), 7.58 (d, 1H, Ar-H), 7.83 (d, 2H, Ar-H), 8.93 (s, 1H, Ar-H); MS: m/z 319.81, C20H21N3O; Analysis: Calcd.: C, 75.21; H, 6.63; N, 13.16. Found: C, 75.03; H, 6.73; N, 13.05.

Workup

  1. customThe solvent was removed under reduced pressure, to the residue 5% sodium carbonate solution
  2. additionwas added
  3. extractionThe product was extracted with ethyl acetate (3×40 mL)
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe product was purified on a column of silica gel

Sources & evidence

ORD record
ord-0013032a8e1c4a6ca76a1cd830066415
Source dataset
uspto-grants-2006_01
Patent number
US06982260B1

Reaction notes

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