Methyl iodide → 6,7-Dimethoxy-2-[4-(1-methyl-2-benzimidazolyl)-1-piperazinyl]-4-quinazolinamine

HRID 1703181Notes

Reaction equation

HRID 1703181 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:25]=[C:24]([NH2:26])[C:23]3[C:18](=[CH:19][C:20]([O:29][CH3:30])=[C:21]([O:27][CH3:28])[CH:22]=3)[N:17]=2)[CH2:12][CH2:11]1.[CH3:31]I>CS(C)=O>[CH3:28][O:27][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][C:20]=1[O:29][CH3:30])[N:17]=[C:16]([N:13]1[CH2:14][CH2:15][N:10]([C:2]3[N:3]([CH3:31])[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:1]=3)[CH2:11][CH2:12]1)[N:25]=[C:24]2[NH2:26]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 130363862-[4-(1H-2-Benzimidazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamine

Product 1

HCID 130616916,7-Dimethoxy-2-[4-(1-methyl-2-benzimidazolyl)-1-piperazinyl]-4-quinazolinamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-[4-(1H-2-benzimidazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamine (0.75 g, described in Example 10) and methyl iodide (1.0 ml) in dimethyl sulfoxide (10 ml) was stirred at room temperature for 4 hr and poured into ice. The resulting mixture was extracted with chloroform. The organic extract was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed through silica gel using 4% methanol in chloroform. The appropriate fractions were combined and evaporated to give a residue (0.42 g) of the title compound. The latter residue was crystallized from hexane-chloroform: mp 249°-251° C.; ir (CHCl3) 3400 and 3300 cm-1 ; uv max (MeOH) 213 (ε=49,870), 250 (ε=64,830); 284 (ε=26,545) and 341 nm (ε=6,565); and Anal. Calcd. for C22H25N7O2 : C, 62.99% H, 6.01% N, 23.37% and Found: C, 62,81% H, 6.18% N, 23.71%.

Workup

  1. additionpoured into ice
  2. extractionThe resulting mixture was extracted with chloroform
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed through silica gel using 4% methanol in chloroform
  8. customevaporated

Sources & evidence

ORD record
ord-fe40937c03df4565822837ca945111d4
Source dataset
uspto-grants-1982_09
Patent number
US04351832

Reaction notes

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