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| | 2,4,7-Trichloropyrido[2,3-d]pyrimidine Basic information |
| Product Name: | 2,4,7-Trichloropyrido[2,3-d]pyrimidine | | Synonyms: | 2,4,7-Trichloropyrido[2,3-d]pyrimidine;2,4,7-Trichloropyrido[2,3...;Pyrido[2,3-d]pyriMidine, 2,4,7-trichloro-;100232;2,4,7-Trichloropyrido[2,3-d]pyrimidine ISO 9001：2015 REACH | | CAS: | 938443-20-0 | | MF: | C7H2Cl3N3 | | MW: | 234.47 | | EINECS: | | | Product Categories: | | | Mol File: | 938443-20-0.mol | ![2,4,7-Trichloropyrido[2,3-d]pyrimidine Structure](CAS/GIF/938443-20-0.gif) |
| | 2,4,7-Trichloropyrido[2,3-d]pyrimidine Chemical Properties |
| Boiling point | 316.4±42.0 °C(Predicted) | | density | 1.685±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | -2.53±0.30(Predicted) | | Appearance | White to off-white Solid | | InChI | InChI=1S/C7H2Cl3N3/c8-4-2-1-3-5(9)12-7(10)13-6(3)11-4/h1-2H | | InChIKey | DNFDLCRLLQVUQK-UHFFFAOYSA-N | | SMILES | C1(Cl)=NC(Cl)=C2C=CC(Cl)=NC2=N1 |
| Hazard Codes | T | | Risk Statements | 25-41 | | Safety Statements | 26-39-45 | | RIDADR | UN 2811 6.1 / PGIII | | WGK Germany | 3 | | HS Code | 2933998090 |
| | 2,4,7-Trichloropyrido[2,3-d]pyrimidine Usage And Synthesis |
| Uses | 2,4,7-Trichloropyrido[2,3-d]pyrimidine is used in the synthetic preparation of dual mTORC1/mTORC2 inhibitors and the discovery of AZD8055 and AZD2014 as potential antitumor agents. | | Synthesis | The general procedure for the synthesis of 2,4,7-trichloropyrido[2,3-d]pyrimidine (Inter.5) using 7-chloropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (Inter.4) as a starting material is as follows: To a stirred anhydrous toluene suspension of 0.5 M Inter.4 (1 equiv.) in an inert atmosphere was slowly added diisopropylethylamine (3 equivalent). The reaction mixture was heated to 70 °C and maintained for 30 min and subsequently cooled to room temperature. Next, phosphorous oxychloride (POCl3, 3 eq.) was added and the reaction mixture was heated to 100 °C for 2.5 hours. Upon completion of the reaction, the mixture was cooled and concentrated under vacuum to give a crude product slurry. The crude product was suspended in ethyl acetate (EtOAc) and filtered through a thin diatomaceous earth pad. The filtrate was concentrated under vacuum to give a brown oil. The oily substance was dissolved in dichloromethane (CH2Cl2) and stirred on silica gel for 30 minutes. Afterwards, the silica gel was removed by filtration and the filtrate was concentrated. The crude product was purified by fast chromatography (silica gel, SiO2) to afford analytically pure 2,4,7-trichloropyrido[2,3-d]pyrimidine (48% yield, 96% purity). Mass spectrometry (LC-MS, ESP) analysis resulted in: m/z 234 [M + H]+, retention time (R/T) = 4.21 min. | | References | [1] Patent: WO2007/60404, 2007, A1. Location in patent: Page/Page column 57; 59
[2] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 101
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1212 - 1216
[4] Patent: WO2008/23161, 2008, A1. Location in patent: Page/Page column 102-103
[5] Patent: CN102887895, 2016, B. Location in patent: Paragraph 0310; 0313; 0314 |
| | 2,4,7-Trichloropyrido[2,3-d]pyrimidine Preparation Products And Raw materials |
| Raw materials | Pyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione-->2,6-Dichloronicotinic acid-->7-Chloropyrido[2,3-d]pyrimidine-2,4-diol-->2-Amino-6-chloronicotinamide-->2-Amino-5-chloropyridine-3-carboxylic acid-->trichlorophosphate-->N,N-Diisopropylethylamine | | Preparation Products | 4-(2,7-dichloropyrido[2,3-d]pyriMidin-4-yl)Morpholine |
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