Sodium hydride → HCID 9804543, compound

HRID 1782076Notes

Reaction equation

HRID 1782076 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:27]=1[N:33]=[C:34]=[S:35]>CN(C=O)C>[CH3:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([CH3:25])[C:27]=1[NH:33][C:34]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1)=[S:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 879762,6-Xylyl isothiocyanateHCID 222439084-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline

Product 1

HCID 9804543HCID 9804543, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (150 mg) in DMF (4.5 ml) was added to sodium hydride (60% dispersion in mineral oil, 0.03 g) and the reaction mixture was stirred at ambient temperature for 20 minutes. 2,6-Dimethylphenyl isothiocyanate (0.162 g) was added and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was evaporated and the residual solid-was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and a 2M solution of ammonia in methanol as eluent. There was thus obtained the title compound (0.112 g); NM Spectrum: (CDCl3) 1.44-1.61 (m, 2H), 1.87-2.08 (m, 5H), 2.32 (s, 3H), 2.36 (s, 6H), 2.94 (d, 2H), 4.04 (m, 5H), 7.1 (s, 1H), 7.19 (m, 3H), 7.29 (s, 1H), 8.69 (s, 1H), 8.9 (s, 1H), 13.37 (s, 1H); Mass Spectrum: M+H+ 466.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 20 hours
  2. customThe reaction mixture was evaporated
  3. customthe residual solid-was purified by column chromatography on silica using
  4. temperatureincreasingly polar mixtures of methylene chloride

Sources & evidence

ORD record
ord-02e849ec93334d6dbdb5ddfd59d5f96a
Source dataset
uspto-grants-2009_03
Patent number
US07498335B2

Reaction notes

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