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CAS No. : | 848369-52-8 | MDL No. : | MFCD07324008 |
Formula : | C10H9ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LTOSAQRHTJQRRM-UHFFFAOYSA-N |
M.W : | 208.64 | Pubchem ID : | 135530878 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 57.09 |
TPSA : | 45.75 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 1.68 |
Log Po/w (WLOGP) : | 1.82 |
Log Po/w (MLOGP) : | 2.04 |
Log Po/w (SILICOS-IT) : | 3.47 |
Consensus Log Po/w : | 2.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.65 |
Solubility : | 0.462 mg/ml ; 0.00222 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.26 |
Solubility : | 1.16 mg/ml ; 0.00556 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.65 |
Solubility : | 0.00467 mg/ml ; 0.0000224 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.94 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P501-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 |
---|---|---|
84% | With chloro-trimethyl-silane In N,N-dimethyl-formamide for 18h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: chloroacetonitrile With sodium In methanol at 20℃; for 1.16667h; Inert atmosphere; Stage #2: 3-methylantranilic acid In methanol at 20℃; for 2h; | Int-A1: 2-(Chloromethyl)-8-methylquinazolin-4(3H)-one Chloroacetonitrile (75 g, 0.99 mol, 3 eq) was added dropwise to a pre-prepared solution of sodium (1.52 g, 6.6 mmol, 0.2 eq) in methanol (200 mL) over 10 mins at RT under a nitrogen atmosphere. After stirring for 1 h, a solution of 2-amino-3-methylbenzoic acid (50 g, 0.33 mmol, 1.0 eq) in methanol (700 mL) was added and the mixture was stirred at RT for another 2 h. The resulting precipitate was collected by filtration and washed with water then MeOH and dried under vacuum to give the title compound (46.9 g, 68%) as a white solid. LCMS: [M+H]+ 209.0. The following intermediates in Table 1 were similarly prepared from the appropriate amino acid starting material according to the method described for Int-A1. |
58% | Stage #1: chloroacetonitrile With sodium In methanol at 25℃; for 0.666667h; Inert atmosphere; Stage #2: 3-methylantranilic acid In methanol at 25℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | Stage #1: 2-sulfanylpyrimidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-(chloromethyl)-8-methylquinazolin-4(3H)-one In N,N-dimethyl-formamide at 20℃; for 0.333333h; | |
36% | Stage #1: 2-sulfanylpyrimidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-(chloromethyl)-8-methylquinazolin-4(3H)-one In N,N-dimethyl-formamide at 20℃; for 0.333333h; | 1 General procedure for synthesis of ((pyrimidin-2-ylthio)methyl)quinazolin-4(3H)-ones: General procedure: The appropriate thiol (2 eqv.) and sodium hydride (2 eqv.) were dissolved in anhydrous DMF and stirred at RT for 20 min. The appropriate quinazolin-4(3H)-one was added as a solid and the reaction mixture stirred at RT for 20 min. Once complete by TLC analysis (100% EtOAc) the reaction was poured over water, isolated, and purified as indicated.Example 1. 8-methyl-2-((pyrimidin-2-ylthio)methyl)quinazolin-4(3H)-one, QDR2: From 2-(chloromethyl)-8- methylquinazolin-4(3H)-one(112 mg, 0.54 mmol); reaction was concentrated in vacuo and product recovered as a white solid; yield 55.3 mg (36%); 1 H NMR (400 MHz, DMSO-c/6) d 12.46 (s, 1 H), 8.70 (d, J = 4.9 Hz, 2H), 7.98 - 7.94 (m, 1 H), 7.70 - 7.64 (m, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.29 (t, J = 4.9 Hz, 1 H), 4.48 (s, 2H), 2.48 (s, 3H); Rt: 5.81 min. HRMS m/z [M+H] + for C14H13N40S: 285.08046, found 285.08128. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 18 h / 90 °C 2: hydrogenchloride / 1,4-dioxane / 125 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1: sulfuric acid / 18 h / 90 °C 2: hydrogenchloride / water; 1,4-dioxane / 125 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ethanol / 95 °C / Inert atmosphere 2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; C31H26NO2P; potassium phosphate / 1,2-dichloro-ethane / 15 h / 50 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With N-ethyl-N,N-diisopropylamine In ethanol at 95℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: acetic acid; sodium cyanoborohydride / methanol; water / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: triethylamine / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 6 h / 20 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 6 h / 20 - 80 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: sodium tris(acetoxy)borohydride / tetrahydrofuran / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / 1-methyl-pyrrolidin-2-one / 1 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere 5: hydrogenchloride / ethyl acetate / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: triethylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / 4 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 2: sodium hydroxide / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere 3: 5 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | Stage #1: S-(3-(hydroxymethyl)cyclohexyl)ethanethioate With sodium hydroxide In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(chloromethyl)-8-methylquinazolin-4(3H)-one In tetrahydrofuran at 20℃; Inert atmosphere; | 70.1 Step 1: 2-(((3-(Hydroxymethyl)cyclohexyl)thio)methyl)-8-methylquinazolin-4(3H)-one To a solution of Int-B13 (316 mg, 1.7 mmol, 1.0 eq) in THF (10 mL) was added 1 M NaOH (4 mL) and the mixture was stirred at RT for 10 min under a N2 atmosphere. Int-A1 (350 mg, 1.7 mmol, 1.0 eq) was then added and the mixture was stirred at RT overnight under a N2 atmosphere. The mixture was diluted with water (5 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (DCM:MeOH, 10:1, v/v) to afford the title compound as a 5:1 mixture of cis/trans isomers (200 mg, 38%) as a white solid. LCMS: [M+H]+ 319.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In N,N-dimethyl-formamide at 20 - 80℃; for 16h; Inert atmosphere; | Intermediate C1: ((8-Methyl-4-oxo-3,4-dihydroquinazolin-2-yl)methyl) ethanethioate To a solution of Int A1 (5.0 g, 24 mmol, 1 eq) in DMF (50 mL) at RT under a N2 atmosphere was added AcSH (3.7 g, 48 mmol, 2 eq) and the mixture was heated at 80° C. for 16 h. After cooling to RT, the mixture was diluted with petroleum ether and the resulting precipitate was collected by filtration and dried to give the title product (6 g, 100%) as a yellow solid, which was used in the subsequent steps without further purification. LCMS: [M+H]+ 249.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With caesium carbonate; sodium iodide In acetone for 2h; Inert atmosphere; Reflux; |