Structure of 1005-38-5
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CAS No. : | 1005-38-5 |
Formula : | C5H6ClN3S |
M.W : | 175.64 |
SMILES Code : | C1=C(N=C(N=C1Cl)SC)N |
MDL No. : | MFCD00006088 |
InChI Key : | ISUXMAHVLFRZQU-UHFFFAOYSA-N |
Pubchem ID : | 70496 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.17 |
TPSA ? Topological Polar Surface Area: Calculated from | 77.1 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.64 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 1.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.44 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.19 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 1.42 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.27 |
Log S (ESOL):? ESOL: Topological method implemented from | -2.35 |
Solubility | 0.78 mg/ml ; 0.00444 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -2.89 |
Solubility | 0.225 mg/ml ; 0.00128 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -2.4 |
Solubility | 0.693 mg/ml ; 0.00394 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -6.19 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 2.04 |
* 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 |
---|---|---|
97.77% | With ammonia; In tetrahydrofuran; at 50 - 60℃; under 5149.01 - 5884.58 Torr;Autoclave; | [00230] Reagents[00231] Experimental procedure:.bul. ; Take ammonia in THF into a 2 L autoclave and add 4, 6-dichloro-2-(Methylthio) pyrimidine slowly..bul. Heat the reaction mixture to 50-60 ° C and maintain the reaction at 50-60 °C for 3-4 hours (Inbuilt pressure 7- 8 Kg/cm )..bul. Check the progress of the reaction by TLC. Upon completion, the reaction was brought to 25-35 ° C..bul. Concentrate the reaction mixture under vacuum..bul. Charge Hexane and stir for 30-45 minutes at 25-35 ° C..bul. Filter the solid and wash the solid with Hexane..bul. Wash the solid with water (2X400 mL)..bul. Dry the solid at 25-35 °C till M.C reaches to less than 2percent.Yield 352.0 gpercent of Yield: 97.77percent.Purity by HPLC: 99.07percent.Other suitable conditions such as ammonia in MeOH or dioxane could be used accordingly when different analogs are used. Example 1- 2. Preparation of 4-Amino-6-chloro-2- meth lthio)pyrimidine, 6.1 |
66% | With ammonia; In water; butan-1-ol; at 20 - 80℃; under 2172.08 Torr; for 0.5h; | 4,6-Dichloro-2-(methylthio)pyrimidine (10 g, 51 mmol) was dissolved in a mixtureButanol/NH4OH (100 ml/50 ml). It was stirred for V2 h in a sealed tube (internal pressure 42 PSI) heated to 8O0C. After cooling to RT, the organic layer was separated, dried over MgSO4 and concentrated. 6.0 g (66percent) of the desired intermediate was obtained as a colourless solid; mlz (ES+) 175, 177 (MH+). |
With ammonia; In water; isopropyl alcohol; at 100℃; for 15h; | Ammonium hydroxide (50 mL) was added to a solution of 4,6-dicloro-2-methylsulfanyl-pyrimidine (1.9 g, 9.7 mmol) in isopropanol (20 mL) in a sealed tube and the resulting mixture was heated to 100° C. for 15 h. The mixture was brought to RT, poured into water and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried and concentrated under vacuum to provide a white solid. MS m/z 176 (MH)+. |
With ammonium hydroxide; In ethanol; water; Petroleum ether; | Part C--4-Amino- 6-chloro-2-(methylthio)pyrimidine A reaction mixture consisting of 124.7 g. (0.64 mole) 4,6-dichloro-2-(methylthio)pyrimidine (prepared as in Part B, above), 500 ml. ethanol, and 250 ml. of substantially saturated aqueous ammonia was heated, with stirring, at 100° C. in an autoclave for 6 hrs. After cooling the reaction mixture, water was added, and a precipitate formed. The precipitate was collected on a filter, and recrystallized from a mixture of ether and petroleum ether to give 40 g. of the desired 4-amino-6-chloro-2-(methylthio)pyrimidine having a melting point at 130° to 131° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In methanol; at 80℃; for 18h; | 6-chloro-2-(methylthio)pyrimidin-4-amine (3.98g, 22.7mmol) is added to a solution of dimethylamine (2.0M in methanol, 2OmL). The mixture is heated to 8O0C for 18h. The reaction is allowed to cool, the precipitate is collected, washed with ethanol, (3.1g, 73percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; In dichloromethane; at 20℃; for 1h; | To a cold stirring solution of 10 g (52.2 mmol) 6-chloro-2- (methylsulfinyl)pyrimidine-4-amine in 450 ml of DCM, 10 g (56.2 mmol) of N- bromosuccinimide were added, and stirring was continued for 1 hour at room temperature to provide 5-bromo-6-chloro-2-(methylthio)pyrimidine-4-amine, which was used without further purification in the next step (see intermediate 3). The end of the reaction is followed by thin layer chromatography. | |
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 0.166667h; | To a cooled solution of 6-chloro-2-(methylthio)pyrimidin-4-amine (15.0 g, 85 mmol) in DM F (150 ml) was added N-bromosuccinimide (16.7 g, 94 mmol) portionwise with stirring at 0 °C. After 10 min the reaction was quenched by the addition of water at 0 °C. The reaction mixture was diluted with brine and extracted 3 times with EtOAc. The combined organic phases were washed twice with saturated aqueous NaHC03solution, then brine, separated, and filtered through a phase separator with Na2S04to dry. The filtrate was concentrated in vacuo to give the title compound (18.8 g, 74 mmol, 80 percent yield, 92percent purity) as colorless solid which was used in the next step without further purification. M/z = 254/256/258 [M+H]+, Rt = 0.95 min (UPLC 2 min), 1 H NMR (600 MHz, DMSO-d6) delta 8.03 (br s, 1 H), 7.25 (br s, 1 H), 2.42 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 135℃; for 5h;Heating / reflux; | Acetic anhydride (10.4 MI, 0. 11 MOL) was added to 6-chloro-2- (methylthio) pyrimidin-4-amine (2.5 g, 0.01 mol) and the reaction mixture was refluxed at 135 °C for 5 hr. The reaction mixture was cooled to room temperature and basified to pH 7 with saturated sodium bicarbonate solution (20 ML). The mixture was partitioned between EtOAc and water, the organic layer was washed with water and brine, dried over MgS04 and concentrated to give the title compound (2.62 g). MS (ES . : 218 (MH+) for C7HGCINO3S |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.9% | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 4h; | To a stirred solution of 10.0 g (57.2 mmol) of 6-chloro-2-(methylthio)pyrimidine-4-amine in 300 ml of dichloromethane were added during 30 minutes a solution of 15.3 g (68.6 mmol) of m-chloroperbenzoic acid (77 percent ) (Aldrich) dissolved in 200 ml of DCM. The reaction mixture was stirred at room temperature for 4 hours. The white precipitate formed was filtered, washed several times with DCM and then after drying gave 10.4 g (94.9 percent) of the intermediate 1.1H-RMN (300 MHz, DMSO-d6): 8 = 3.28 (s, 3H), 6.64 (s, 1H), 8.1 1 (s, 2H). |
1 g | With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 4h; | To a solution of 1.0 g (5.7 mmol) of 6-chloro-2- (methylthio) pyrimidin-4-amine in 50 mL of methylene chloride was added 1.5 g (6.9 mmol) M-chloroperbenzoic acid (77percent) solution.The reaction mixture was stirred for 4 hours at room temperature.The resulting white precipitate was filtered, washed with methylene chloride several times, dried,1.0 g of intermediate (F) was obtained |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With N,N-dimethyl-aniline; trichlorophosphate; for 1h;Reflux; | General procedure: 2-Alkylthio-4-amino-6-hydroxylpyrimidine (2a,b) (27 mmol), POCl3 (15 mL, 162 mmol), and PhNMe2 (6.8 mL, 54 m mol) were refluxed together for 1 h. The excess POCl3 was removed in vacuo, and then the residue was poured into 60 mL (1:1, v/v) of cooled concentrated ammonium hydroxide and chloroform. The solution was kept stirring at room temperature. After POCl3 was dissolved completely, the aqueous phase was extracted with CHCl3 (3.x.20 mL), the combined organic phases were dried with MgSO4, concentrated, and purified by flash column chromatography (Et3N-neutralized silica gel, gradient elution separation with EtOAc/P.E., 1:50-1:2, v/v) and then by recrystallization from cyclohexane to afford the product as colorless crystals. |
Tags: 1005-38-5 synthesis path| 1005-38-5 SDS| 1005-38-5 COA| 1005-38-5 purity| 1005-38-5 application| 1005-38-5 NMR| 1005-38-5 COA| 1005-38-5 structure
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H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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The concentration of the dissolution solution you need to prepare is mg/mL