[ CAS No. 61727-34-2 ] {[proInfo.proName]}

Name: 61727-34-2|Ethyl 2-(4-chloro-2-(methylthio)pyrimidin-5-yl)acetate|97%
Brand: Ambeed
SKU: A256060
Price: 11.0 USD
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3d Animation Molecule Structure of 61727-34-2

Structure of 61727-34-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 61727-34-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 61727-34-2 ]

SDS Specification

Alternatived Products of [ 61727-34-2 ]

Product Details of [ 61727-34-2 ]

CAS No. :	61727-34-2	MDL No. :	MFCD11977460
Formula :	C₉H₁₁ClN₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NJCDAOMVXVONIU-UHFFFAOYSA-N
M.W :	246.71	Pubchem ID :	295792
Synonyms :

Calculated chemistry of [ 61727-34-2 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.44
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.44
TPSA :	77.38 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	2.16
Log Po/w (WLOGP) :	1.96
Log Po/w (MLOGP) :	1.1
Log Po/w (SILICOS-IT) :	2.61
Consensus Log Po/w :	2.02

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.7
Solubility :	0.496 mg/ml ; 0.00201 mol/l
Class :	Soluble
Log S (Ali) :	-3.42
Solubility :	0.0943 mg/ml ; 0.000382 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.66
Solubility :	0.0542 mg/ml ; 0.00022 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.2

Safety of [ 61727-34-2 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P264-P270-P301+P310+P330-P405-P501	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 61727-34-2 ]

* 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.

Upstream synthesis route of [ 61727-34-2 ]
Downstream synthetic route of [ 61727-34-2 ]

[ 61727-34-2 ] Synthesis Path-Upstream 1~4

1
[ 29571-44-6 ]
[ 61727-34-2 ]

Yield	Reaction Conditions	Operation in experiment
95.5%	for 4 h; Reflux	Step 3: Ethyl [4-chl oro-2-(methylthio)pyrimidin-5-yl 1 acetate; A mixture of ethyl [2-(methylthio)-4-oxo-1,4-dihydropyrimidin-5-yl]acetate (28.8 g, 0.128 mol) in POCl₃ (240 mL) was refluxed for 4 hours and then concentrated under reduced pressure. The residue was twice re-evaporated with benzene and purified by column chromatography on silica gel (ethyl acetate-hexanes, 1 :3) to afford ethyl [4-chloro-2-(methylthio)pyrimidin-5-yl]acetate (29.72 g, 95.5percent yield).¹HNMR (400 MHz, CDCl₃) δ: 8.32 (s, 1 H), 4.13 (q, J- 5.7 Hz, 2 H), 3.62 (s, 2 H), 2.52 (s, 3 H), 1.21 (t, J= 5.7, 3 H).
94%	for 4 h; Reflux	A mixture of 120 (28.8 g, 0.128 mol) in phosphoryl chloride (240 mL) is stirred under refiux for 4 hours After cooling to room temperature, the mixture is concentrated, coevaporated with benzene twice, and purified by silica gel column chromatography (EA:hexanes = 1:3) to give 121 as a yellow oil (29.7 g, 94percent yield). (MS: [M+Hj1 247.1)
93%	for 2 h; Reflux	General procedure: A mixture of compound 1 (X = H, Me, Ph, SMe; Y = H,R1 = Et) and phosphoryl chloride was refluxed for 2 h.Phosphoryl chloride was then evaporated. Dichloromethane(DCM) and water was added to the dark oilyresidue. It was cooled to 5–10 C and ammonium hydroxidesolution was added until pH 9–10. The layers wereseparated and the aqueous layer was extracted with DCM.The combined organic layer was washed with aqueousNaHCO3 solution (10 percent) and brine. It was dried andevaporated to give compounds 7

Reference： [1] Patent: WO2009/152027, 2009, A1, . Location in patent: Page/Page column 22; 25
[2] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0374
[3] Monatshefte fur Chemie, 2016, vol. 147, # 4, p. 767 - 773
[4] Patent: WO2016/22644, 2016, A1, . Location in patent: Page/Page column 73

2
[ 5472-38-8 ]
[ 61727-34-2 ]

Reference： [1] Monatshefte fur Chemie, 2016, vol. 147, # 4, p. 767 - 773
[2] Patent: WO2016/22644, 2016, A1,
[3] Patent: WO2009/152027, 2009, A1,

3
[ 123-25-1 ]
[ 61727-34-2 ]

Reference： [1] Patent: WO2016/22644, 2016, A1,
[2] Patent: WO2017/176812, 2017, A1,
[3] Patent: WO2009/152027, 2009, A1,

4
[ 14273-44-0 ]
[ 61727-34-2 ]

Reference： [1] Patent: WO2017/176812, 2017, A1,

[ 61727-34-2 ] Synthesis Path-Downstream 1~37

2
[ 61727-34-2 ]
[ 74-88-4 ]
[ 1201362-85-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃;	Step 4: Ethyl 2-[4-chloro-2-(methylthio)pyrimidin-5-yl]-2-methylpropanoate; A solution of <strong>[61727-34-2]ethyl [4-chloro-2-(methylthio)pyrimidin-5-yl]acetate</strong> (150 g, 608 mmol) and methyl iodide (259 g, 1824 mmol) in N,N-dimethylformamide (2 L) was cooled to 0 C and sodium hydride (60 wt%, 60.8 g, 1520 mmol) was added over ninety minutes. The cooling bath was removed upon completion of the addition and the reaction mixture was allowed to warm to <n="28"/>room temperature overnight. Excess base was quenched by the addition of 7% aqueous citric acid solution (150 mL); the resulting mixture was poured into an extractor containing water (5 L) and extracted with diethyl ether 4 times. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated to give a dark reddish oil. This crude oil was purified by chromatography using a 1.5 kg silica column (1: 19 ethyl acetate-heptane, grading to 1 :3 ethyl acetate-heptane) to give 2~[4-chloro-2-(methylthio)pyrirnidin~5-yl]-2- methylpropanoate (151.8 g, 91% yield) Calcd for C11H15ClN2O2S [M+l]+: 275, Found: 275

Reference： [1]Patent: WO2009/152027,2009,A1 .Location in patent: Page/Page column 22; 25-26

3
[ 29571-44-6 ]
[ 61727-34-2 ]

Yield	Reaction Conditions	Operation in experiment
95.5%	With trichlorophosphate; for 4.0h;Reflux;	Step 3: Ethyl [4-chl oro-2-(methylthio)pyrimidin-5-yl 1 acetate; A mixture of ethyl [2-(methylthio)-4-oxo-1,4-dihydropyrimidin-5-yl]acetate (28.8 g, 0.128 mol) in POCl3 (240 mL) was refluxed for 4 hours and then concentrated under reduced pressure. The residue was twice re-evaporated with benzene and purified by column chromatography on silica gel (ethyl acetate-hexanes, 1 :3) to afford ethyl [4-chloro-2-(methylthio)pyrimidin-5-yl]acetate (29.72 g, 95.5% yield).1HNMR (400 MHz, CDCl3) delta: 8.32 (s, 1 H), 4.13 (q, J- 5.7 Hz, 2 H), 3.62 (s, 2 H), 2.52 (s, 3 H), 1.21 (t, J= 5.7, 3 H).
94%	With trichlorophosphate; for 4.0h;Reflux;	A mixture of 120 (28.8 g, 0.128 mol) in phosphoryl chloride (240 mL) is stirred under refiux for 4 hours After cooling to room temperature, the mixture is concentrated, coevaporated with benzene twice, and purified by silica gel column chromatography (EA:hexanes = 1:3) to give 121 as a yellow oil (29.7 g, 94% yield). (MS: [M+Hj1 247.1)
93%	With trichlorophosphate; for 2.0h;Reflux;	General procedure: A mixture of compound 1 (X = H, Me, Ph, SMe; Y = H,R1 = Et) and phosphoryl chloride was refluxed for 2 h.Phosphoryl chloride was then evaporated. Dichloromethane(DCM) and water was added to the dark oilyresidue. It was cooled to 5-10 C and ammonium hydroxidesolution was added until pH 9-10. The layers wereseparated and the aqueous layer was extracted with DCM.The combined organic layer was washed with aqueousNaHCO3 solution (10 %) and brine. It was dried andevaporated to give compounds 7

With trichlorophosphate; for 2.0h;Reflux;

Step C: Ethyl [4-chloro-2-(methylsulfanvl)pvrimidin-5-vnacetate A stirred suspension of ethyl [4-hydroxy-2-(methylsulfanyl)pyrimidin-5-yl]acetate (15.0 g, 65.7 mmol) in POCI3 (123 mL) was heated at reflux for 2 h, then concentrated in vacuo. The residue was twice resuspended in benzene (50 mL) and concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc - 100:0 to 25:75, to give the title compound. MS: m/z = 247.0 (M + 1).

Reference： [1]Patent: WO2009/152027,2009,A1 .Location in patent: Page/Page column 22; 25
[2]Patent: WO2017/176812,2017,A1 .Location in patent: Paragraph 0374
[3]Monatshefte fur Chemie,2016,vol. 147,p. 767 - 773
[4]Patent: WO2016/22644,2016,A1 .Location in patent: Page/Page column 73

4
[ 61727-34-2 ]
C₂₃H₂₉N₇O₂ [ No CAS ]