Phosphorus oxychloride → 2-Chloro-4-neopentylamino-6-nitroquinazoline

HRID 1250563

Reaction equation

HRID 1250563 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:18])=O.[CH2:21]([NH2:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>O>[Cl:18][C:9]1[N:8]=[C:7]([NH:26][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 79882NeopentylamineHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 183263792-Chloro-4-neopentylamino-6-nitroquinazoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 367 mg (1.77 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione was added 15.13 g (98.70 mmol) of phosphorus oxychloride to effect reaction in the same manner as in Example 10. Next, to the reaction mixture was added dropwise 309 mg (3.54 mmol) of neopentylamine under ice cooling, and the resulting mixture was stirred under ice cooling for 2 hours. Water was added to the reaction mixture, and crystals thus precipitated were filtered out to obtain 2-chloro-4-neopentylamino-6-nitroquinazoline. The compound was dissolved in 2 ml of DMF, and after 1.52 g (26.65 mmol) of allylamine was added to the resulting solution, the mixture was stirred at room temperature for 2.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 210 mg (yield: 37.6%) of the title compound.

Workup

  1. customreaction in the same manner as in Example 10
  2. customthus precipitated
  3. filtrationwere filtered out

Sources & evidence

ORD record
ord-0e13dbc75b8543418dff0d8b97e2279b
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Linked notes

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