Dimethyl Sulfone → 2,4-Diamino-5-methylquinazoline-6-carbonitrile

HRID 653536Notes

Reaction equation

HRID 653536 reaction equation
[C:1]([C:3]1[C:9]([CH3:10])=[C:8]([C:11]#[N:12])[CH:7]=[CH:6][C:4]=1[NH2:5])#[N:2].Cl.Cl[C:15]([NH2:17])=[NH:16].CS(C)(=O)=O.[OH-].[Na+]>O>[NH2:17][C:15]1[N:16]=[C:1]([NH2:2])[C:3]2[C:4](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[C:9]=2[CH3:10])[N:5]=1

Participants

6

Reactant 4

HCID 6213Dimethyl SulfoneHCID 14798Sodium HydroxideHCID 3084509Chloroformamidinium chlorideHCID 13885404HCID 13885404, compound

Product 1

HCID 138854082,4-Diamino-5-methylquinazoline-6-carbonitrileYield 43.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.3 g (1.91 mmol) of 2,4-dicyano-3-methylaniline, 0.44 g (3.82 mmol) of chloroformamidine hydrochloride, and 0.7 g of dimethylsulfone was heated to 170°-175° C. The mixture solidified after a time, and was allowed to cool to room temperature. Water (20 ml) was added, and the resulting mixture was made basic with 1 molar aqueous sodium hydroxide solution, filtered, and washed with water. The solids were triturated with methanol to yield 0.167 g of 2,4-diamino-5-methyl-6-quinazolinecarbonitrile, mp>270° C. The infrared, mass, and proton magnetic resonance spectra corresponded to those of a known sample of the compound.

Workup

  1. temperaturewas heated to 170°-175° C
  2. filtrationfiltered
  3. washwashed with water
  4. customThe solids were triturated with methanol

Sources & evidence

ORD record
ord-aa481005c3ed4f19bc72491e7818d2d7
Source dataset
uspto-grants-1987_06
Patent number
US04677219

Reaction notes

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