2-氨基嘧啶

2-氨基嘧啶
別名	2-嘧啶胺
識別
CAS號	109-12-6
PubChem	7978
SMILES	Nc1ncccn1;
InChI	1S/C4H5N3/c5-4-6-2-1-3-7-4/h1-3H,(H2,5,6,7);
InChIKey	LJXQPZWIHJMPQQ-UHFFFAOYSA-N
性質
化學式	C4H5N3
摩爾質量	95.1 g·mol−1
外觀	白色至淺黃色粉末
熔點	125 °C
沸點	157 °C（135 torr）
溶解性	可溶於水和甲醇
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

2-氨基嘧啶是一種有機化合物，化學式為C₄H₅N₃。它是可溶於水的白色固體。它可由2-氯嘧啶或2-溴嘧啶的氨化反應得到。^[6]^[7]

反應

2-氨基嘧啶在乙醇中可被碘甲烷甲基化，產率90%。碘甲烷在苯中和氨基鋰存在下可再次甲基化反應產生的2-(甲氨基)嘧啶，但產率較低，只有31%。^[8]

它和N-溴代丁二醯亞胺在乙酸銨的存在下於乙腈中反應，可以得到2-氨基-5-溴嘧啶。^[9]

參考文獻

^ ^1.0 ^1.1 Entry from 2-Aminopyrimidine from TCI Europe, retrieved on 2017-11-10
^ 來源：Sigma-Aldrich Co., product no. A78608 .
^ R. L. Shivalkar, S. V. Sunthankar. Reaction of Lithium Aluminum Hydride with Arylaminomethylenemalonate Esters and Related Compounds 1. Journal of the American Chemical Society. 1960-02, 82 (3): 718–721 [2021-10-23]. ISSN 0002-7863. doi:10.1021/ja01488a053. （原始內容存檔於2021-10-23）（英語）.
^ Tsukamoto, Tadashi; Takebe, Saburo. Pure 2-aminopyrimidine. 1959 JP 34000533 B.
^ Datenblatt 2-Aminopyrimidine bei AlfaAesar, abgerufen am {{{Abruf}}}.
^ Chengwen Xue, Jiesheng Li, Jin Ping Lee, Ping Zhang, Jie Wu. Continuous amination of aryl/heteroaryl halides using aqueous ammonia in a Teflon AF-2400 tube-in-tube micro-flow reactor. Reaction Chemistry & Engineering. 2019, 4 (2): 346–350 [2021-10-23]. ISSN 2058-9883. doi:10.1039/C8RE00216A （英語）.
^ Mohammed K. Elmkaddem, Cédric Fischmeister, Christophe M. Thomas, Jean-Luc Renaud. Efficient synthesis of aminopyridine derivatives by copper catalyzed amination reactions. Chem. Commun. 2010, 46 (6): 925–927 [2021-10-23]. ISSN 1359-7345. doi:10.1039/B916569J （英語）.
^ Overberger, C. G.; Kogon, Irving C. Monomer Synthesis. Methylation of 2-Aminopyrimidine 1. Journal of the American Chemical Society. 1954, 76 (4): 1065–1068. ISSN 0002-7863. doi:10.1021/ja01633a040.
^ Jason J. Hanthorn, Luca Valgimigli, Derek A. Pratt. Preparation of Highly Reactive Pyridine- and Pyrimidine-Containing Diarylamine Antioxidants. The Journal of Organic Chemistry. 2012-08-17, 77 (16): 6908–6916 [2021-10-23]. ISSN 0022-3263. doi:10.1021/jo301013c （英語）.

[TCI-1] 1.0 ^1.1 Entry from 2-Aminopyrimidine from TCI Europe, retrieved on 2017-11-10

[Sigma-2] 來源：Sigma-Aldrich Co., product no. A78608 .

[3] R. L. Shivalkar, S. V. Sunthankar. Reaction of Lithium Aluminum Hydride with Arylaminomethylenemalonate Esters and Related Compounds 1. Journal of the American Chemical Society. 1960-02, 82 (3): 718–721 [2021-10-23]. ISSN 0002-7863. doi:10.1021/ja01488a053. （原始內容存檔於2021-10-23）（英語）.

[4] Tsukamoto, Tadashi; Takebe, Saburo. Pure 2-aminopyrimidine. 1959 JP 34000533 B.

[Alfa-5] Datenblatt 2-Aminopyrimidine bei AlfaAesar, abgerufen am {{{Abruf}}}.

[6] Chengwen Xue, Jiesheng Li, Jin Ping Lee, Ping Zhang, Jie Wu. Continuous amination of aryl/heteroaryl halides using aqueous ammonia in a Teflon AF-2400 tube-in-tube micro-flow reactor. Reaction Chemistry & Engineering. 2019, 4 (2): 346–350 [2021-10-23]. ISSN 2058-9883. doi:10.1039/C8RE00216A （英語）.

[7] Mohammed K. Elmkaddem, Cédric Fischmeister, Christophe M. Thomas, Jean-Luc Renaud. Efficient synthesis of aminopyridine derivatives by copper catalyzed amination reactions. Chem. Commun. 2010, 46 (6): 925–927 [2021-10-23]. ISSN 1359-7345. doi:10.1039/B916569J （英語）.

[8] Overberger, C. G.; Kogon, Irving C. Monomer Synthesis. Methylation of 2-Aminopyrimidine 1. Journal of the American Chemical Society. 1954, 76 (4): 1065–1068. ISSN 0002-7863. doi:10.1021/ja01633a040.

[9] Jason J. Hanthorn, Luca Valgimigli, Derek A. Pratt. Preparation of Highly Reactive Pyridine- and Pyrimidine-Containing Diarylamine Antioxidants. The Journal of Organic Chemistry. 2012-08-17, 77 (16): 6908–6916 [2021-10-23]. ISSN 0022-3263. doi:10.1021/jo301013c （英語）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]