Dimethyl Sulfone → 6-Chloropyrido[3,2-d]pyrimidine-2,4-diamine

HRID 1517428Notes

Reaction equation

HRID 1517428 reaction equation
[NH2:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Cl.Cl[C:13]([NH2:15])=[NH:14].CS(C)(=O)=O.[OH-].[Na+]>O>[NH2:15][C:13]1[N:14]=[C:9]([NH2:10])[C:3]2[N:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 6213Dimethyl SulfoneHCID 14798Sodium HydroxideHCID 5927503-Amino-6-chloropyridine-2-carbonitrileHCID 3084509Chloroformamidinium chloride

Product 1

HCID 133817146-Chloropyrido[3,2-d]pyrimidine-2,4-diamineYield 68.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

A mixture consisting of 3-amino-6-chloro-pyridine-2-carbonitrile (4.6 g, 30 mmol), chloroformamidine hydrochloride (6.9 g, 60 mmol) and dimethylsulfon (12 g) was heated at 165° C. for 30 minutes. After cooling to room temperature, water (500 ml) was added. The solution was neutralized with a 30% NaOH solution to pH 9-10. The precipitate was filtered off, washed with water, dried over P2O5, resulting in the pure title compound as a yellow solid (4.0 g, yield: 68%) which was characterised as follows:

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-d12007e81ee84e268be9e5b50b0dca3b
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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