Alternatived Products of [ 52128-35-5 ]
Product Details of [ 52128-35-5 ]
| CAS No. : | 52128-35-5 |
MDL No. : | MFCD00866404 |
| Formula : |
C19H23N5O3
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | NOYPYLRCIDNJJB-UHFFFAOYSA-N |
| M.W : |
369.42
|
Pubchem ID : | 5583 |
| Synonyms : |
CI-898
|
Chemical Name : | 5-Methyl-6-(((3,4,5-trimethoxyphenyl)amino)methyl)quinazoline-2,4-diamine |
Application In Synthesis of [ 52128-35-5 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 52128-35-5 ]
| Yield | Reaction Conditions | Operation in experiment |
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5 Anhydrous Trimetrexate
Anhydrous Trimetrexate Anhydrous trimetrexate was prepared by dehydrating trimetrexate monohydrate. A sample of trimetrexate monohydrate (about 30 g) was placed in a Petri dish and dried in a vacuum dessicator over phosphorus pentoxide. The sample was dried at a pressure of about 100 microns for 6 days. |
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2 6.7.2.
6.7.2. STEP 1: TRIMETREXATE BASE, CRUDE The reactor is charged with 41.5 L of n-butanol and 10.4 L of deionized water. 6.3 kg of crude trimetrexate acetate is then added. Then, 3 g of sodium metabisulfite, 0.65 L of ammonia, 1 kg of tonsil and 1 kg of Supercel are added. The reaction mixture is heated to 90° C. to a gentle reflux, and stirred for 10 minutes. Thereafter, a pressure filtration is performed with a preheated filter tube at about 1 bar, into PE-drums. The tube is rinsed afterwards with a mixture of 4 L of n-butanol and 1 L of deionized water. The filtrate is transferred into the cleaned reactor (cleaned by rinsing with 5 liters of a 4:1 n-butanol/deionized water mixture) and heated to 70° C. 1.95 L of ammonia is then added. The base crystallizes after about 5 minutes. The reaction mixture is cooled to 20° C. and filtered using vacuum. The filter cake is washed with 5 L of deionized water and 5 L of ethanol (80%, using 4 parts by volume ethanol and one part by volume of water). The yield is about 5.6 kg of humid substance, or 4.4+-0.5 kg of dried product (calculated), corresponding to a yield of 84+-10% relative to crude trimetrexate acetate. |
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[ 253-82-7 ]
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[ 24313-88-0 ]
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[ 18917-72-1 ]
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[ 52128-35-5 ]
| Yield | Reaction Conditions | Operation in experiment |
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With hydrogen; acetic acid;aluminum nickel; In water; ethyl acetate; N,N-dimethyl-formamide; |
Step B Synthesis of 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyphenylamino)methyl]<strong>[253-82-7]<strong>[253-82-7]qui</strong>nazoline</strong> (Compound 93) A mixture of 1.1 grams (0.005 mole) of 2,4-diamino-6-cyano-5-methyl<strong>[253-82-7]<strong>[253-82-7]qui</strong>nazoline</strong>, 4.6 grams (0.025 mole) 3,4,5-trimethoxyaniline and 2.0 grams (catalyst) of Raney nickel (50% slurry in water) in 30 mL of water and 70 mL of acetic acid was hydrogenated at 50 psi of hydrogen for 6 hours using a Parr hydrogenator. After this time the reaction mixture was filtered. The filter cake was slurried with a boiling mixture of 15 mL of water and 35 mL of acetic acid and was then filtered. The filtrates were combined and subjected to thin layer chromatography (TLC). The TLC analysis indicated that a small amount of the starting <strong>[253-82-7]<strong>[253-82-7]qui</strong>nazoline</strong> remained unreacted. The filtrate was combined with 1.0 gram of Raney nickel and the mixture was again hydrogenated for an additional 1.5 hours using the Parr hydrogenator. After this time the reaction mixture was filtered and concentrated under reduced pressure to a residual oil. The residual oil was subjected to column chromatography on silica gel. Elution was accomplished initially using 25% N,N-dimethylformamide in ethyl acetate and, finally 40% N,N-dimethylformamide in ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure to a residual solid. The solid was recrystallized from water, yielding 0.5 gram of 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyphenylamino)methyl]<strong>[253-82-7]<strong>[253-82-7]qui</strong>nazoline</strong>, mp 95-210 C. The NMR analysis was consistent with the proposed structure; however, it indicated that the compound was a complex with acetic acid and water. NOTE: The compound of Example 14 is known in the literature as Trimetrexate, for use in treatments of certain kinds of cancers. [J. Med. Chem., 26, 1753-1760 (1983)] |
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