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| | 6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione Basic information |
| Product Name: | 6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione | | Synonyms: | AURORA KA-4912;1,3-DIMETHYL-6-AMINOURACIL;1,3-DIMETHYL-4-AMINOURACIL;1,3-DIMETHYL-2,6-DIOXO-4-AMINOTETRAHYDROPYRIMIDINE;4-AMINO-1,3-DIMETHYLURACIL FOR SYNTHESIS;6-AMINO-1,3-DIMETHYLURICIL;6-AMINO-1,3-DIMETHYL-1,2,3,4-TETRAHYDROPYRIMIDINE-2,4-DIONE;2,4(1H,3H)-Pyrimidinedione, 6-amino-1,3-dimethyl- | | CAS: | 6642-31-5 | | MF: | C6H9N3O2 | | MW: | 155.15 | | EINECS: | 229-662-0 | | Product Categories: | Amines;Building Blocks;Heterocyclic Building Blocks;Pyrimidines;bc0001 | | Mol File: | 6642-31-5.mol |  |
| | 6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione Chemical Properties |
| Melting point | 295 °C (dec.) (lit.) | | Boiling point | 243.1±43.0 °C(Predicted) | | density | 1.288±0.06 g/cm3(Predicted) | | vapor pressure | 0Pa at 25℃ | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | 6g/l | | form | Solid | | pka | 5.17±0.70(Predicted) | | color | Pale Beige | | PH | 6.9 (100g/l, H2O, 20℃) | | Water Solubility | 7.06g/L(25 ºC) | | InChI | 1S/C6H9N3O2/c1-8-4(7)3-5(10)9(2)6(8)11/h3H,7H2,1-2H3 | | InChIKey | VFGRNTYELNYSKJ-UHFFFAOYSA-N | | SMILES | CN1C(N)=CC(=O)N(C)C1=O | | LogP | -0.4 at 20℃ | | CAS DataBase Reference | 6642-31-5(CAS DataBase Reference) | | EPA Substance Registry System | 2,4(1H,3H)-Pyrimidinedione, 6-amino-1,3-dimethyl- (6642-31-5) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 22-26-36/37/39 | | WGK Germany | 1 | | RTECS | YQ8755000 | | TSCA | TSCA listed | | HS Code | 29335990 | | Storage Class | 11 - Combustible Solids |
| | 6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione Usage And Synthesis |
| Chemical Properties | Crystallizes (water). Melting point 295°C (293°C). Decomposes. | | Uses | 6-Amino-1,3-dimethyluracil is used as a reagent in the synthesis of new pyrimidine and caffeine derivatives that display highly potential antitumor activity. It is also used as a starting material in the synthesis of fused pyrido-pyrimidines. | | Synthesis | General procedure for the synthesis of 1,3-dimethyl-6-aminouracil from 4-amino-2,6-dihydroxypyrimidine and iodomethane: 4-amino-2,6-dihydroxypyrimidine (1.27 g, 10 mmol) was added to a pre-heated ethanol solution (50 ml) containing KOH (0.56 g, 10 mmol) and heated continuously for 40 min. After completion of the reaction, the mixture was cooled to room temperature followed by addition of iodomethane (20 mmol). The reaction mixture was stirred under heating conditions for 8 hours, after which it was cooled to room temperature. The reaction mixture was poured into cold distilled water (100 ml) to induce precipitation of the final product 1,3-dimethyl-6-aminouracil. The precipitate was collected by filtration and washed with distilled water (100 ml). Finally, recrystallization from methanol gave 1,3-dimethyl-6-aminouracil in yellow crystalline form. | | References | [1] Letters in Drug Design and Discovery, 2015, vol. 12, # 6, p. 471 - 478
[2] DRP/DRBP Org.Chem.,
[3] Patent: CN104744471, 2016, B. Location in patent: Paragraph 0026; 0027; 0028 |
| | 6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione Preparation Products And Raw materials |
| Raw materials | Acetic anhydride-->1,3-Dimethylurea-->2-cyano-N-methyl-N-[(methylamino)carbonyl]acetamide-->6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde-->Solvent Yellow 93-->6-Aminouracil-->5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one-->Iodomethane-->Cyanoacetic acid-->Ethanol | | Preparation Products | 1,3,7-Trimethyluric acid-->Nifekalant hydrochloride-->6-Amino-5-(2-chloro-acetyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione-->4,6-Dimethyl-1H-1,2,3-triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione-->2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-6-[(3,4,5,6-tetrahydro-2H-azepin-7-yl)amino]--->Methanimidamide, N,N-dimethyl-N'-(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-4-pyrimidinyl)--->8-Dimethylaminotheophylline |
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