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CAS No. : | 18592-13-7 | MDL No. : | MFCD00010095 |
Formula : | C5H5ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VCFXBAPEXBTNEA-UHFFFAOYSA-N |
M.W : | 160.56 | Pubchem ID : | 73273 |
Synonyms : |
6- (Chloromethyl)uracil
|
Chemical Name : | 6-(Chloromethyl)pyrimidine-2,4(1H,3H)-dione |
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 : | 2.0 |
Molar Refractivity : | 37.45 |
TPSA : | 65.72 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) : | -7.81 cm/s |
Log Po/w (iLOGP) : | 0.77 |
Log Po/w (XLOGP3) : | -0.75 |
Log Po/w (WLOGP) : | -0.35 |
Log Po/w (MLOGP) : | -0.42 |
Log Po/w (SILICOS-IT) : | 2.19 |
Consensus Log Po/w : | 0.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.74 |
Solubility : | 29.2 mg/ml ; 0.182 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.15 |
Solubility : | 113.0 mg/ml ; 0.703 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.48 |
Solubility : | 0.537 mg/ml ; 0.00334 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.82 |
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 |
---|---|---|
90.8% | With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 2 h; Reflux | In a 250 mL three-necked flask,Compound 2 (11.5 g, 0.081 mol) was added,Then, 115 mL of dichloromethane was added successively,Thionyl chloride (17.6 mL, 0.24 mol) and a catalytic amount of N, N-dimethylformamide,Add the temperature to reflux and stir the reaction for 2 hours.Cooled to room temperature,Filter,Dichloromethane wash,dry,11.8 g of 6-chloromethyluracil was obtained in a yield of 90.8percent. |
55.56% | With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3 h; Large scale | In a 500 L reactor, compound 2 (8.0 kg, 56.29 mol) was added to 80 L of methylene chloride, stirred and 8 L of dichlorosulfoxide was added at room temperature (20 C)Keep slowly at room temperature dropwise 4L DMF, the solution becomes clear, the reaction 3h, a large number of white solid precipitation.The 2-point reaction of the TLC following compound disappeared (dichloromethane: methanol = 5: 1) and the reaction was completed. The reaction solution was centrifuged, The filter cake was air-dried for 6 hours at 60 ° C to afford SM1 as an off-white solid (5.0 kg, 55.56percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With n-butyllithium In ethanol; hexane at -75 - 20℃; for 3 h; Inert atmosphere | At room temperature,The 500mL of tetrahydrofuran and 50g compound IV 'has added to the three bottles,After sufficiently stirring, the mixture was replaced with nitrogen three times,Ethanol bath temperature of liquid nitrogen in the range of -80 ~ -75 ,80 mL of a n-butyllithium n-hexane solution (2.5 M) was slowly added under the condition of securing the gas-tightness,The reaction was stirred at a temperature of 2 h,And then gradually increased to room temperature reaction 1h.The reaction was quenched with an appropriate amount of saturated ammonium chloride solution,And then extracted with methyl tert-butyl ether,Washed repeatedly with purified water and then with absolute ethanol,Drying after blowing a yellow-white solid 21.8g,I.e. Compound IV,Yield 78percent. |
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