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CAS No. : | 873-83-6 | MDL No. : | MFCD00006071 |
Formula : | C4H5N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LNDZXOWGUAIUBG-UHFFFAOYSA-N |
M.W : | 127.10 | Pubchem ID : | 70120 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 32.09 |
TPSA : | 91.74 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) : | -8.23 cm/s |
Log Po/w (iLOGP) : | 0.11 |
Log Po/w (XLOGP3) : | -1.62 |
Log Po/w (WLOGP) : | -1.35 |
Log Po/w (MLOGP) : | -1.36 |
Log Po/w (SILICOS-IT) : | 0.64 |
Consensus Log Po/w : | -0.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.1 |
Solubility : | 101.0 mg/ml ; 0.793 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.2 |
Solubility : | 203.0 mg/ml ; 1.6 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -1.07 |
Solubility : | 10.9 mg/ml ; 0.0857 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
69% | With sodium In ethanolReflux | General procedure: Compounds 1a, 1b and 1e were prepared according to the reportedmethods26–34 by the addition of urea, methylurea and/or methylthiourea (0.1 mol) to ethyl cyanoacetate (0.1 mol) in absolute ethanol(290 mL) containing sodium (0.2 mol). The mixture was refluxed for10–12 h, allowed to cool to r.t. and acidified with acetic acid (pH 6).The resulting precipitate was washed with distilled water and dried in adesiccator overnight.1a: Yield 69percent; m.p. > 360 °C (lit. ≥ 360 °C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With acetic anhydride; sodium hydroxide In neat (no solvent) for 0.166667 h; Microwave irradiation | We have found that the microwave assisted of reaction urea (1 mmol) with cyano acetic acid (1 mmol) under solvent-free conditions results in rapid formation of the corresponding Amino uracil (Figure1).The products were easily obtained by addition of water to the reaction mixture and recrystalization of crude products from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: for 3 h; Reflux Stage #2: at 20℃; for 72 h; |
6-Aminouracil (5) (5.18 g, 40.7 mmol) was suspended in HM DS (25 mL) and H2S04 (0.1 m L) was added. The mixture was heated at reflux for 3 h then concentrated in vacuo. The residue was dissolved in DM F (30 mL), Mel (8.5 mL, 136.5 mmol) was added, and stirring was continued for 72 h at room temperature. The reaction was cooled to 0 °C and NaHC03 was carefully added. The mixture was stirred at 0 °C until no more bubbling was observed. The precipitate was filtered, washed with MeOH and H20 and dried to give the title compound 6 (4.49 g, 78percent) as a yellow solid which was used without further purification.Rf 0.23 (EtOAc-MeOH-N H4OH, 7:2.7:0.3);H NMR (400 MHz, DMSO-d6) δ 10.36 (1H, s, Ntf), 6.16 (2H, s, Ntf2), 4.56 (1H, s, tf-5); 3.04 (3H, s, NCtf3); 13C NMR (100 M Hz, DMSO-d6) δ 163.3 (C-4), 153.5 (C-6), 151.1 (C-2), 74.0 (C-5), 25.9 (NCH3);MP Lit: 327 °C19, found: 320-323 °C; |
42.6% | Stage #1: for 6 h; Reflux Stage #2: at 40℃; for 16 h; |
Step 1 6-amino-3-methylpyrimidine-2,4(lH,3H)-dione To a solution of the 6-aminopyrimidine-2,4(lH,3H)-dione (15 g, 1 18 mmol) in 1 ,1 ,1 ,3,3,3- hexamethyldisilazane (50 mL) was added ammonium sulfate(0.671g, 5 mmol), then the resulting mixture was heated to reflux with stirring for 6 h. The mixture was concentrated to give a light-yellow solid. This solid was combined with acetonitrile (50 mL) and iodomethane (15 mL, 250 mmol) was added. The resulting mixture was stirred at 40 °C for 16 h. Then the mixture was concentrated, neutralized with saturated sodium bicarbonate to pH =7, filtered, and the filter cake was washed with brine and ethanol, dried under vacuum to give 6-amino-3- methylpyrimidine-2,4 (lH,3H)-dione (7.1 g, 42.6 percent yield) as yellow solid. LCMS MH+ 142. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: With potassium hydroxide In ethanol for 0.666667 h; Heating Stage #2: for 8 h; Heating |
To a heated ethanolic KOH solution (0.56 g, 10 mmol in 50 ml ethanol) compound 1 (1.27 g, 10 mmol) was added and heating was continuous for 40 min. The mixture was allowed to cool to room temperature, and methyl iodide (20 mmol) was added. The mixture was stirred under heating for 8 h and then allowed to cool to room temperature and finally poured into cold H2O (100 ml), The final product ppt. was filtered and washed with 100 ml H2O and crystallized from methanol to afford 2 as yellow crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium acetate In water at 72 - 80℃; for 1 h; | To a suspended solution of 6-aminouracil (32, 6.35 g, 50.0 mmol) and sodium acetate (4.10 g, 50.0 mmol) in H20 (50 mL) at a temperature of 72 °C was added a solution of chloroacetaldehyde (50percent in water, 11.8 g, 75.2 mmol) drop-wise. The reaction mixture was heated to 80 °C and stirring was continued for 60 mm. After cooling the reaction mixture to room temperature, the resulting solid was collected by filtration, washed with water and acetone, and dried under vacuum to afford 33 as a light-brown solid (6.46 g, 86percent). ‘H-NMR (400 MHz, DMSO-d6) ö 11.45 (s, 1H), 11.10 (s, 1H), 10.48 (s, 1H), 6.64-6.51 (m, 1H), 6.22 (t, J = 2.5 Hz, 1H); MS (m/z) [M+Hj 152.06. |
33% | With sodium acetate In water for 3 h; Heating / reflux | A solution of commercially available 6-amino-1 H-pyrimidine-2,4-dione (25 g, 0.2 mol) and NaOAc (20 g, 0.24 mol) in 1.25 L of distilled water was treated with chloroacetaldehyde (25 ml_, 50percent w/w in water). After 3 h at reflux, the reaction mixture was filtered while still warm, to remove the brown solid. The yellow mother liquor was cooled to RT then acidified to pH ~ 4 by addition of 2.5 M HCI. The desired product (9.722 g, 33percent) was isolated by filtration and finally dried in the oven. 1H NMR (cfe-DMSO) δ 11.46 (1 H, br s), 11.11 (1 H, br s), 10.49 (1 H, br s), 6.57 (1 H, dd, J = 2.0, 3.6 Hz), 6.22 (1 H, dd, J = 2.0, 3.2 Hz). |
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