Sodium hydride → HCID 23507938, compound

HRID 1654389Notes

Reaction equation

HRID 1654389 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.[H-].[Na+].[CH3:20][O:21][CH2:22]Br>CN(C=O)C.O>[CH3:1][C:2]1[N:11]([CH2:20][O:21][CH3:22])[C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 135622202HCID 135622202, compound

Product 1

HCID 23507938HCID 23507938, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3,9-dimethylbenzo[f]quinazolin-1(2H)-one (1.0 g, 4.5 mmol) in DMF (25 ml) was added 80% NaH (0.15 g, 5.0 mmol) (Aldrich) portion wise and the mixture was stirred 35 minutes. Bromomethyl methyl ether (0.39 ml, 4.8 mmol) (Aldrich) was added in one portion and the solution was stirred at room temperature overnight. The solution was then diluted with water (100 ml) and extracted twice with methylene chloride (100, 40 ml). The combined methylene chloride extracts were washed with a small volume of water, dried (K2CO3), and concentrated in vacuo. The residue was purified by silica gel (4 0 g) chromatography eluting with ethyl acetate:methylene chloride (0 to 1:19) to give 3,9-dimethyl-2-methoxymethylbenzo[f]quinazolin-1(2H)-one and the corresponding O-alkylated material in a 4:1 ratio as determined by NMR (0.79 g). 1H NMR (DMSO-d6, 300 MHz) for major isomer δ: 2.57 (s, 3H, C9 --CH3), 2.68 (s, 3H, C3 --CH3), 3.38 (s, 3H, OCH3), 5.62 (s, 2H, NCH2O), 7.51 (dd, J=8,2 Hz, 1H, Ar), 7.56 (d, J=9 Hz, 1H, Ar), 7.96 (d, J=8 Hz, 1H, Ar), 8.24 (d, J=9 Hz, 1H, Ar), 9.63 (s, 1H, Ar). Anal. Calculated for C16H16N2O2 : C, 71.62; H, 6.01; H, 10.44. Found: C, 71.55; H, 6.03; H, 10.43.

Workup

  1. stirringthe solution was stirred at room temperature overnight
  2. extractionextracted twice with methylene chloride (100, 40 ml)
  3. washThe combined methylene chloride extracts were washed with a small volume of water
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel (4 0 g) chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-27c38ec0aa464a05b74be5b5084c05b7
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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