2-Amino-4-chloropyrimidine synthesis
- Product Name:2-Amino-4-chloropyrimidine
- CAS Number:3993-78-0
- Molecular formula:C4H4ClN3
- Molecular Weight:129.55
3934-20-1
7461-50-9
3993-78-0
2,4-Dichloropyrimidine (1.0 g, 6.7 mmol) was used as starting material and 28% w/v aqueous ammonium hydroxide solution (20 mL) was added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. The obtained residue was dried and subsequently purified by fast column chromatography (FCC) with the eluent being chloroform solution containing 2-10% ethanol, resulting in the isolation of 2-amino-4-chloropyrimidine and 2-chloro-4-aminopyrimidine. Product yields: 200 mg of 2-amino-4-chloropyrimidine in 23% yield and 600 mg of 2-chloro-4-aminopyrimidine in 69% yield.
108-53-2
256 suppliers
$5.00/100mg
3993-78-0
319 suppliers
$8.00/1g
Yield:3993-78-0 73%
Reaction Conditions:
with chlorosulfonic acid;trichlorophosphate at -5 - 90; for 5 h;Inert atmosphere;
Steps:
4.2.9. 4-Chloro-2-pyrimidinamine (7)
In a three neck 250 mL round bottom flask equipped with reflux condenser was added isocytosine (20 g, 0.18 mol) followed by phosphorus oxychloride (40 mL, 0.43 mol) at -5 °C and under an atmosphere of nitrogen. To this was cautiously added chlorosulfonic acid (4 mL, 0.06 mol). The solution was permitted to heat spontaneously to room temperature and then heated at 45 °C for 1 h. It was then heated cautiously at 90 °C for 4 h, before it was cooled to room temperature. The mixture was then cooled in an ice bath before it was pour onto 400 mL of ice water with vigorous stirring. Adjusted the pH to 7 with ammonia water (28% by weight) (temperature was held below 20 °C). A tan colored solid was collected by filtration. The solid was dried to afford 4-chloro-2-pyrimidinamine (17 g, 73% yield) as an off white solid. m.p. 166-167 °C.
References:
Pan, Li;Jiang, Ying;Liu, Zhen;Liu, Xing-Hai;Liu, Zhuo;Wang, Gang;Li, Zheng-Ming;Wang, Di [European Journal of Medicinal Chemistry,2012,vol. 50,p. 18 - 26] Location in patent:experimental part
108-53-2
256 suppliers
$5.00/100mg
3993-78-0
319 suppliers
$8.00/1g
97229-11-3
198 suppliers
$22.00/100mg
3993-78-0
319 suppliers
$8.00/1g
3934-20-1
728 suppliers
$9.00/1g
3993-78-0
319 suppliers
$8.00/1g