ChemicalBook CAS DataBase List 2-Amino-4-chloropyrimidine

2-Amino-4-chloropyrimidine synthesis

7synthesis methods

Product Name:2-Amino-4-chloropyrimidine
CAS Number:3993-78-0
Molecular formula:C4H4ClN3
Molecular Weight:129.55

108-53-2 Synthesis

108-53-2
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$5.00/100mg

3993-78-0
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$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

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3934-20-1 Synthesis