5-amino-6-methyl-3-phenyl-4(3H)-pyrimidinone | 65765-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-amino-6-methyl-3-phenyl-4(3H)-pyrimidinone
• 英文别名: 5-amino-6-methyl-3-phenylpyrimidin-4(3H)-one；5-amino-6-methyl-3-phenyl-4(3H)-pyrimidone；5-amino-6-methyl-3-phenyl-4(3H)pyrimidone；5-aminopyrimidin-4(3H)-one；5-amino-6-methyl-3-phenyl-3H-pyrimidin-4-one；5-Amino-6-methyl-3-phenyl-4(3H)-pyrimidinon；5-amino-6-methyl-3-phenylpyrimidin-4-one
• CAS: 65765-92-6
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: GNZWOWZHWAQYOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-6-methyl-3-phenyl-4(3H)-pyrimidinone 在 氯化亚砜 作用下， 以 水 为溶剂， 反应 18.0h， 生成 4-formamido-3-(N-methyl)carbamoylisothiazole
  参考文献：
  名称：

  A Novel Formation of 3,4-Disubstituted Isothiazoles from 5-Amino-6-methylpyrimidinones

  摘要：

  DOI：

  10.1016/s0040-4020(01)81673-2
• 作为产物：
  描述：

  4-氨基安替比林 在 sodium hydroxide 作用下， 以 xylene 为溶剂， 以40%的产率得到5-amino-6-methyl-3-phenyl-4(3H)-pyrimidinone
  参考文献：
  名称：

  Udea, Taisei; Oda, Noriichi; Ito, Isoo, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 7, p. 2144 - 2147

  摘要：

  DOI：

文献信息

• A facile ring transformation of 5-aminopyrimidin-4(3H)-one into 2-alkoxy-1H-imidazoles in the presence of oxidative metal salts and alkyl alcohols
  作者：Izumi Matsuura、Taisei Ueda、Nobutoshi Murakami、Shin-ichi Nagai、Jinsaku Sakakibara

  DOI：10.1039/c39910001688

  日期：——

  5-Amino-6-methyl-3-phenylpyrimidin-4(3H)-one 1 was transformed into 2-alkoxy-1H-imidazoles 2a–f by treatment with various oxidative metal salts such as CuCl2, CuBr2, Cu(NO3)2, CuSO4, Tl(NO3)3, FeCl3 and Pb(OAc)4 in alkyl alcohols.

  在烷基醇中，以多种氧化性金属盐如CuCl2、CuBr2、Cu(NO3)2、CuSO4、Tl(NO3)3、FeCl3和Pb(OAc)4处理5-氨基-6-甲基-3-苯基嘧啶-4(3H)-酮1，可将其转化为2-烷氧基-1H-咪唑2a-f。
• Ring Transformation Mediated by Lewis Acids and Oxidizing Agents. Synthesis of 2-Methoxy-1H-imidazole from 5-Aminopyrimidin-4(3H)-one.
  作者：Izumi MATSUURA、Taisei UEDA、Nobutoshi MURAKAMI、Shin-ichi NAGAI、Jinsaku SAKAKIBARA

  DOI：10.1248/cpb.41.608

  日期：——

  Treatment of 5-aminopyrimidln-4(3H)-one (1) with Lewis acidic metal salts such as zinc chloride, zinc bromide, zinc iodide, aluminum chloride, aluminum bromide, nickel chloride, copper(I) chloride, or copper(I) iodide in the presence of oxidizing agents such as ceric ammonium nitrate, ammonium persulfate, or phenyliodine(III) diacetate in methanol gave 2-methoxy-1H-imidazole (2).

  用路易斯酸性金属盐（如氯化锌、溴化锌、碘化锌、氯化铝、溴化铝、氯化镍、氯化铜(I)或碘化铜(I)）处理5-氨基嘧啶-4(3H)-酮（1），并在甲醇中加入氧化剂（如铈铵硝酸盐、过硫酸铵或二醋酸苯碘（III）），得到了2-甲氧基-1H-咪唑（2）。
• Electrochemical transformation of 5-aminopyrimidin-4(3H)-one: indirect anodic oxidation mediated by electrochemically generated chlorine
  作者：Izumi Matsuura、Taisei Ueda、Nobutoshi Murakami、Shin-ichi Nagai、Jinsaku Sakakibara、Yukihisa Kurono、Keiichiro Hatano

  DOI：10.1039/c39920000828

  日期：——

  Anodic oxidation of 5-amino-6-methyl-3-phenylpyrimidin-4(3H)-one 1 conc. HCI–MeOH gave 2-(formamido)-2-methoxy-3-oxobutananilide 2(the crystal structure of which has been determined) and 3-(N-chloroimino)-2-(formamido)-2-methoxybutananilide 3via cleavage of the C(2)–N(3) bond and the migration of C(2) to the 5-amino group by the mediation of electrochemically generated chlorine.

  5-amino-6-methyl-3-phenylpyrimidin-4(3H)-one 1 conc.HCI-MeOH 阳极氧化得到 2-（甲酰氨基）-2-甲氧基-3-氧代丁酰苯胺 2（其晶体结构已经确定）和 3-（N-氯亚氨基）-2-（甲酰氨基）-2-甲氧基丁酰苯胺 3，这是通过电化学产生的氯的中介作用，C(2)-N(3) 键断裂，C(2) 迁移到 5-氨基基团上。
• Synthesis of 5-amino-4(3H)-pyrimidinones. II. Synthesis of 5-acyl- and 5-alkylamino-3-phenyl-6-methyl-4(3H)-pyrimidinones and determination of their analgesic and antiinflammatory activities.
  作者：TAISEI UEDA、JINSAKU SAKAKIBARA、JOZI NAKAGAMI

  DOI：10.1248/cpb.31.4263

  日期：——

  N-Acylation and N-alkylation of 5-amino-6-methyl-3-phenyl-4 (3H)-pyrimidinone (I) were carried out and the products were examined for analgesic and antiinflammatory activities. The reaction of I with α-bromopropionyl bromide or chloroacetyl chloride followed by treatment with 40% aqueous dimethylamine gave 5-(α-dimethylaminopropionamido)- or 5-(N, N-dimethylglycyl) amino-6-methyl-3-phenyl-4 (3H)-pyrimidinone (IIc or IIe). The reaction of 3, 4-dihydro-1, 6-dimethyl-5-dimethylamino-4-oxo-3-phenylpyrimidinium iodide (IV) with several alkylamines such as propylamine, isobutylamine, sec-butylamine, and allylamine in acetonitrile gave 5-alkylamino-3, 4-dihydro-1, 6-dimethyl-4-oxo-3-phenylpyrimidinium iodides (IVa-d), whose reduction with sodium borohydride in methanol gave 5-alkylamino-1, 2-dihydro-1, 6-dimethyl-3-phenyl-4 (3H)-pyrimidinones (VIIa-d). The reaction of I with benzaldehyde or p-methoxybenzaldehyde gave 5-benzylidene (or p-methoxybenzylidene) amino-6-methyl-3-phenyl-4 (3H)-pyrimidinones (VIIIa, b). Compounds I and VIIIa showed analgesic and antiinflammatory activities in mice and rats.

  对5-氨基-6-甲基-3-苯基-4(3H)-嘧啶酮(I)进行N-酰化和N-烷基化，并检测产物的镇痛和抗炎活性。 I与α-溴丙酰溴或氯乙酰氯反应，然后用40%二甲胺水溶液处理，得到5-(α-二甲基氨基丙酰胺基)-或5-(N,N-二甲基甘氨酰)氨基-6-甲基-3-苯基-4 (3H)-嘧啶酮（IIc 或 IIe）。 3, 4-二氢-1, 6-二甲基-5-二甲基氨基-4-氧代-3-苯基吡啶鎓碘化物 (IV) 与几种烷基胺如丙胺、异丁胺、仲丁胺和烯丙胺在乙腈中反应，得到 5-烷基氨基-3, 4-二氢-1, 6-二甲基-4-氧代-3-苯基吡啶鎓碘化物 (IVa-d)，用硼氢化钠在甲醇中还原，得到 5-烷基氨基-1, 2-二氢-1, 6-二甲基-3-苯基-4(3H)-嘧啶酮(VIIa-d)。 I与苯甲醛或对甲氧基苯甲醛的反应得到5-苯亚甲基(或对甲氧基苯亚甲基)氨基-6-甲基-3-苯基-4(3H)-嘧啶酮(VIIIa，b)。化合物 I 和 VIIIa 在小鼠和大鼠中显示出镇痛和抗炎活性。
• Novel utilization of organoselenium compounds. I. A facile transformation of fused isoselenazoles to fused pyridines.
  作者：Taisei Ueda、Yoshitsugu Shibata、Jinsaku Sakakibara

  DOI：10.1248/cpb.33.3065

  日期：——

  A facile transformation of 7-oxo-6-phenyl-6H-isoselenazolo [4, 3-d]-pyrimidine (2) or 4, 5-dihydro-4-methyl-6-oxo-5-phenyl-6H-pyrazolo [4, 3-c]-isoselenazole (5) into pyrido [3, 2-d] pyrimidines (3a-f) or pyrazolo [4, 3-b] pyridines (6a-f) was carried out by reactions using active methylene compounds such as malononitrile, ethyl cyanoacetate, ethyl acetoacetate, ethyl malonate, and cyanoacetamide in the presence of a catalytic amount of sodium ethoxide in ethanol.

  将 7-氧代-6-苯基-6H-异硒唑并 [4, 3-d] -嘧啶 (2) 或 4, 5-二氢-4-甲基-6-氧代-5-苯基-6H-吡唑并 [4, 3-c] -异硒唑 (5) 简单转化为吡啶并 [3, 2-d] 嘧啶 (3a-f) 或吡唑并 [4、3-b]吡啶（6a-f）的反应是在乙醇中乙醇钠催化剂存在下，使用丙二腈、氰乙酸乙酯、乙酰乙酸乙酯、丙二酸乙酯和氰乙酰胺等活性亚甲基化合物进行的。