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CAS No. : | 67449-23-4 | MDL No. : | MFCD02167411 |
Formula : | C9H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WFDHXKXFTSQIMG-UHFFFAOYSA-N |
M.W : | 176.17 | Pubchem ID : | 334023 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 50.16 |
TPSA : | 65.72 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.57 cm/s |
Log Po/w (iLOGP) : | 1.29 |
Log Po/w (XLOGP3) : | 1.13 |
Log Po/w (WLOGP) : | 0.52 |
Log Po/w (MLOGP) : | 0.92 |
Log Po/w (SILICOS-IT) : | 2.65 |
Consensus Log Po/w : | 1.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.21 |
Solubility : | 1.08 mg/ml ; 0.00612 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.1 |
Solubility : | 1.39 mg/ml ; 0.00787 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.53 |
Solubility : | 0.0524 mg/ml ; 0.000297 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.57 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
79% | at 100℃; for 6 h; | 8-methylquinazoline-2,4(1H,3H)-dione (4.50 g, 25.50 mmol) was added to a mixture of phosphorus oxychloride (47.6 mL, 510.9 mmol). The resulting mixture was stirred at 100 °C for 6 hours before it was allowed to cool to ambient temperature. The mixture was slowly poured into water (300 mL) at 40 °C maintaining the internal temperature below 60 °C. Aprecipitate was formed and collected by filtration to provide 2,4-dichloro-8-methylquinazoline (4.30 g, 79percent). |
78% | for 3 h; Reflux | General procedure: Quinazolin-2,4(1H,3H)-dione (10 g, 61.7 mmol), DIPEA (22.6 ml, 129 mmol) and POCl3 (4.0 ml) were heated at reflux. After 3 hours the reaction mixture was cautiously poured over crushed ice and stirred vigorously. This aqueous mixture was extracted with CH2Cl2 DCM and the combined organic layers were washed with brine and dried over Na2SO4. Evaporation of the solvent gave a crystalline solid that was dissolved in CH2Cl2 after which it was filtered over a pad of silica using CH2Cl2 as eluent. Removal of the organic phase gave the product as 10.80 g (54.3 mmol, 88percent) of a white solid. |
5.28 g | With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline for 4 h; Reflux | <Step 2> 2,4-dichloro-8-methylquinazoline A mixture of 8-methylquinazoline-2,4(1H,3H)-dione (4.88 g, 27.7 mmol) prepared in Step 1, N,N-dimethylaniline (2.8 ml, 22.2 mmol) and phosphorus oxychloride (28 ml) was stirred at reflux for 4 hours. After cooling the reaction mixture to room temperature, the reaction mixture was added into ice water. The resulting solid was filtered, washed with water, and dried in vacuo to give the titled compound (5.28 g) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.12 (d, 1H), 7.83 (d, 1H), 7.62 (t, 1H), 2.75 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: at 160℃; for 6 h; Stage #2: at 100℃; for 0.0833333 h; |
General procedure: 2-Amino-3-methylbenzoic acid (5.0 g, 33.1 mmol) and urea (20 g) were stirred at 160oC. After 6 hours the mixture was cooled to 100oC and an equivalent volume of water was added while stirring was continued for 5 minutes. The formed precipitate was filtered off and washed with water to yield a solid cake that was suspended in a solution of 0.5 N NaOH in water. The suspension was heated to boil for 5 minutes and then cooled to r.t. The pH was adjusted to 2 with concentrated HCl and the quinazoline-dione was filtered off. After washing with water:methanol (1:1) the product was dried in vacuo to yield 4.50 g (25.5 mmol, 77percent) of a solid; 1H-NMR (CDCl3) δ (ppm) 7.78-7.74 (m, 1H), 7.49-7.46 (m, 1H), 7.11-7.05 (m, 1H), 2.31 (s, 3H). |
74% | at 150℃; | A suspension of 2-amino-3-methylbenzoic acid (5.20 g, 34.40 mmol) and urea (4.87 mL, 107.33 mmol) in NMP (50 mL) was heated to 150 °C overnight. The resulting solution was cooled to ambient temperature and poured into ice-water (50 mL) and stirred until the ice melted. The white solid was collected by filtration, washed with water (3 x 30 mL) and dried over night to afford 8-methylquinazoline-2,4(1H,3H)-dione (4.50 g, 74percent) as a beige solid. |
4.88 g | at 190℃; for 4 h; | <Step 1> 8-methylquinazoline-2,4(1H,3H)-dione A mixture of 2-amino-3-methylbenzoic acid (5 g, 33.1 mmol) and urea (5.96 g, 99.2 mmol) was stirred at 190° C. for 4 hours. After cooling the reaction solution to room temperature, water (70 ml) was added thereto and the reaction solution was stirred for 1 hour. The resulting solid was filtered and dried in vacuo to give the titled compound (4.88 g) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.29 (brs, NH), 10.42 (brs, NH), 7.77 (d, 1H), 7.48 (d, 1H), 7.10 (t, 1H), 2.35 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With urea In ethanol | EXAMPLE 2 8-Methyl-2,4-(1H,3H)quinazolinedione 3-Methylanthranilic acid (15 g., 0.1 mole), urea (36 g., 0.6 mole) and phenol (86 g.) were mixed together and heated to reflux for three hours. The reaction was then allowed to cool to 100° C. and ethanol (75 ml.) added dropwise. The resulting solid was filtered and washed twice with cold ethanol to afford 13.2 g. (75percent yield); m.p. 170° C. |
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