2-氨基嘧啶

2-氨基嘧啶
别名	2-嘧啶胺
识别
CAS号	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
性质
化学式	C4H5N3
摩尔质量	95.1 g·mol−1
外观	白色至浅黄色粉末
熔点	125 °C
沸点	157 °C（135 torr）
溶解性	可溶于水和甲醇
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

2-氨基嘧啶是一种有机化合物，化学式为C₄H₅N₃。它是可溶于水的白色固体。它可由2-氯嘧啶或2-溴嘧啶的氨化反应得到。^[6]^[7]

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反应

2-氨基嘧啶在乙醇中可被碘甲烷甲基化，产率90%。碘甲烷在苯中和氨基锂存在下可再次甲基化反应产生的2-(甲氨基)嘧啶，但产率较低，只有31%。^[8]

它和N-溴代丁二酰亚胺在乙酸铵的存在下于乙腈中反应，可以得到2-氨基-5-溴嘧啶。^[9]

参考文献

[1]
Entry from 2-Aminopyrimidine from TCI Europe, retrieved on 2017-11-10
[2]
来源：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. （原始内容存档于2021-10-23）（英语）.
[4]
Tsukamoto, Tadashi; Takebe, Saburo. Pure 2-aminopyrimidine. 1959 JP 34000533 B.
[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 （英语）.
[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 （英语）.
[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 （英语）.

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

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

[3] [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. （原始内容存档于2021-10-23）（英语）.

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

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

[6] [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 （英语）.

[7] [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 （英语）.

[8] [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] [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 （英语）.

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