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CAS No. : | 6972-82-3 | MDL No. : | MFCD00091924 |
Formula : | C5H8N4O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PSIJQVXIJHUQPJ-UHFFFAOYSA-N |
M.W : | 156.14 | Pubchem ID : | 157184 |
Synonyms : |
5,6-Diamino-1-methyluracil
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 41.39 |
TPSA : | 106.9 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.25 cm/s |
Log Po/w (iLOGP) : | 0.28 |
Log Po/w (XLOGP3) : | -1.4 |
Log Po/w (WLOGP) : | -1.75 |
Log Po/w (MLOGP) : | -1.5 |
Log Po/w (SILICOS-IT) : | -0.76 |
Consensus Log Po/w : | -1.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.33 |
Solubility : | 73.1 mg/ml ; 0.468 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.34 |
Solubility : | 70.8 mg/ml ; 0.454 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.3 |
Solubility : | 78.8 mg/ml ; 0.505 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.03 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.3% | With hydrogen In isopropyl alcohol at 55℃; for 2 h; | To further increase the conversion rate of the reaction, Catalytic reduction of 6-amino-5-nitroso-1-methyluracil The reaction system of 5,6-diamino-1-methyluracil was optimized, and in order to obtain a high separation yield, the post-reaction treatment was also optimized. The optimized steps were: 1) 0.4 g of ammonium metatungstate modified palladium metal catalyst (prepared in Example 1), Substrate 6-amino-5-nitroso-1-methyl uracil 10.0g was added to 80ml of isopropanol and stirred in the hydrogenation reactor; 2) Nitrogen replaces the air in the hydrogenation reactor three times, and then adjusts the temperature of the hydrogenation reactor to 55°C. (Hydrogen pressure is 0.3 MPa), the reaction was taken 2h after the reaction solution was subjected to HPLC (HPLC assay result was 99.6percent conversion, selectivity 98.3percent), stirring was stopped, hydrogen pressure was removed, and the temperature was lowered to room temperature; 3) Filtrate, remove the catalyst by filtration, collect the filtrate and heat up to 50-60 °C (after treatment; 4) Add purified water to the post-treatment solution, stop the dripping when turbidity has appeared, and incubate for 2h, then continue dropping. When water is no longer crystallized (a total of 45 ml of water is dropped, 10 ml is added when turbid, and 35 ml is added dropwise), the temperature is lowered to 10° C., filtered and dried to give pale yellow 5,6-diamino-1 -methyl uracil ( The weight yield was 92.3percent, and the volume purity was 99.4percent). |
87.9% | at 25 - 60℃; for 7 h; | 6-Amino-5-nitroso-1-methyluracil 2a (11.50 g, 67.6 mmol) was dissolved in 200 mL of aqueous ammonia (25percent)in,Sodium dithionite (41.20 g, 236.6 mmol) was added at room temperature 25 ° C and stirred. The temperature in the reaction flask was gradually increased to 35 °C. When the temperature inside the bottle no longer rises, it is heated to 60 ° C and stirred for 1 h.The reaction was then moved to room temperature and stirred for 6 h. After the reaction was completed, the stirring was stopped, filtered, and the cake was washed with ice water and dried in vacuo. Intermediate 3a was obtained as a white solid 9.28 g, yield 87.9percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With hydrogenchloride; sodium nitrite In water at 0 - 25℃; for 2 h; | 6-Amino-1-methylpyrimidine-2,4-dione (10.0 g, 70.1 mmol) was dissolved in water (100 mL). Hydrochloric acid (7 mL, 84.0 mmol, 12 N) was added dropwise at 0°C while stirring. Then sodium nitrite (5.80 g, 84.2 mmol) was dissolved in water (50 mL) and added dropwise to the reaction solution to give a purple precipitate. The reaction was stirred at 25°C for 2 hours, filtered and washed with cold water to give a purple solid. The solid was dissolved in water (100 mL) and sodium hydrosulphite (18.7 g, 118 mmol) was added in batches while stirring, heated to 60°C and stirred for 0.5 h, cooled to 25°C and stirred for 16 h, filtered, washed with cold water (50 mL), ethanol (50 mL), acetone (50 mL) respectively, and dried to give 5,6-diamino-1-methylpyrimidine-2,4-dione (8.60 g, as a pale yellow solid) with a yield of 93percent. 1H NMR (400 MHz, DMSO-d6) δ 10.49(br, 1H), 6.15(br, 2H), 3.25(s, 3H), 2.95(br, 2H). MS-ESI calcd. [M + H]+ 157, found 157. |
93% | With hydrogenchloride; sodium nitrite In water at 0 - 25℃; for 2 h; | 6-Amino-1-methylpyrimidin-2,4-dione (10.0 g, 70.1 mmol) was dissolved in water (100 mL), and then hydrochloric acid (7 mL, 84.0 mmol, 12N) was added dropwise at 0° C. while stirring. Sodium nitrite (5.80 g, 84.2 mmol) was dissolved in water (50 mL), which was added dropwise into the reactants, then a purple precipitate appeared. The reaction solution was stirred 25° C. for 2 hours, the then was filtered. The filtrate was washed with cold water to give a purple solid. The solid was dissolved in water (100 mL), and then sodium hypodisulfite (18.7 g, 118 mmol) was added in batches while stirring. The reaction solution was heated to 60° C. and stirred for 0.5 hour, and then was cooled to 25° C. and stirred for 16 hours. The reaction solution was filtered and the filtrate was washed with water (50 mL), ethanol (50 mL) and propanone (50 mL), respectively, followed by drying to give a product 5,6-diamino-1-methylpyrimidin-2,4-dione (8.60 g, pale yellow solid), with a yield of 93percent. 1H NMR (400 MHz, DMSO-d6) δ10.49 (s, 1H), 6.15 (s, 2H), 3.25 (s, 3H), 2.95 (s, 2H). MS-ESI calculated value: [M+H]+ 157; measured value: 157. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.1% | Stage #1: at 105℃; for 3 h; Stage #2: With sodium hydroxide In water at 105℃; for 1 h; |
5,6-Diamino-1-methyluracil 3a (10.00 g, 64.0 mmol) was dissolved in formic acid (3.305 mL) and water(74.74 mL) in a mixed solvent,After heating at 105 ° C for 3 h, the temperature was lowered to 20 ° C.Add sodium hydroxide (5.12g,A solution of 128.1 mmol of water (6.40 mL) was heated at 105 ° C for 1 h and then the reaction was completed. Cool to 0 ° C, adjust the pH to 4 with glacial acetic acid, precipitate a yellow-white solid, filter, wash the filter cake with ice water,Drying in vacuo gave Intermediate 4a as a white solid (10.01 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: for 2 h; Reflux Stage #2: With sodium hydroxide In water at 100℃; for 16 h; Stage #3: at 66℃; for 3 h; |
Synthesis of 8-bromo-3-methyl-1H-purine-2,6(3H,7H)-dione The title compound was prepared by adding to 5,6-diamino-1-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (3 g, 19.2 mmol) to 50 ml H2O and 1.02 ml (26.9 mmol) formic acid. The reaction mixture was refluxed for 2 h and 3 ml 1 N NaOH was added and the temperature was kept at 100 °C for 16 h. After cooling to 0°C in an ice bath the reaction mixture was acidified with acetic acid to pH = 6. The resulting solid was filtered off and washed with H2O and dried to give 2.5 g (15 mmol, 78percent) of the product. The crude product was dissolved in 50 ml acetic acid and 2.47 g (30.1 mmol) sodium acetate was added. After addition of 0.925 ml (18.06 mmol) bromine the reaction mixture was stirred for 3 h at 66°C. The suspension was cooled to RT, filtered off and washed with acetic acid (1x), H2O (4x) and Ether (2x). The resulting solid was dried to give a yellowish solid. Yield: 3.11 g (84 percent). LCMS (method 2): Rt = 0.420 min; MS (ESIpos) m/z = 245.0 [M]+, 247.0 [M+2H]+. 1H NMR (300 MHz, DMSO- d6) δ = 11.20 (s, 1 H), 3.31 (s, 3H). |
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