[ CAS No. 1979-96-0 ] {[proInfo.proName]}

Name: 1979-96-0|4,6-Dichloro-2-(methylthio)-5-nitropyrimidine|98%
Brand: Ambeed
SKU: A231111
Price: 6.0 USD
Availability: InStock
Rating: 96 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 1979-96-0

Structure of 1979-96-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 1979-96-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1979-96-0 ]

SDS Specification

Alternatived Products of [ 1979-96-0 ]

Product Details of [ 1979-96-0 ]

CAS No. :	1979-96-0	MDL No. :	MFCD02323208
Formula :	C₅H₃Cl₂N₃O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GHAWBARMICSLQS-UHFFFAOYSA-N
M.W :	240.07	Pubchem ID :	11345458
Synonyms :

Calculated chemistry of [ 1979-96-0 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.59
TPSA :	96.9 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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.37
Log Po/w (XLOGP3) :	2.8
Log Po/w (WLOGP) :	2.41
Log Po/w (MLOGP) :	1.14
Log Po/w (SILICOS-IT) :	0.75
Consensus Log Po/w :	1.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.3
Solubility :	0.12 mg/ml ; 0.000499 mol/l
Class :	Soluble
Log S (Ali) :	-4.49
Solubility :	0.00774 mg/ml ; 0.0000322 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.77
Solubility :	0.408 mg/ml ; 0.0017 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.23

Safety of [ 1979-96-0 ]

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:

Application In Synthesis of [ 1979-96-0 ]

* 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 [ 1979-96-0 ]
Downstream synthetic route of [ 1979-96-0 ]

[ 1979-96-0 ] Synthesis Path-Upstream 1~4

1
[ 67-56-1 ]
[ 1979-96-0 ]
[ 56032-35-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	at 20℃; for 6 h;	Na2CO3 (0.49 g, 4.62 mmol) was added to a soln of pyrimidine 717(1.0 g, 4.16 mmol) in MeOH (30 mL), and the mixture was stirredat r.t. for 6 h. H2O (150 mL) was added and the resulting precipitate was collected by filtration, dried, and crystallized (hexane) to givea colorless solid; yield: 0.63 g (64percent); mp 78–79 °C (Lit.19 77.5–79.5 °C).1H NMR (300 MHz, CDCl3): δ = 2.60 (s, 3 H, SCH3), 4.13 (s, 3 H,OCH3).13C NMR (75 MHz, CDCl3): δ = 14.8, 56.2, 128.8, 151.4, 160.9,173.8.Anal. Calcd for C6H6ClN3O3S: C, 30.58; H, 2.57. Found: C, 30.75;H, 2.54.

Reference： [1] Synthesis (Germany), 2013, vol. 45, # 17, p. 2438 - 2446

2
[ 67-56-1 ]
[ 124-41-4 ]
[ 1979-96-0 ]
[ 56032-35-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 20℃; for 3 h;	Step 3: A mixture of 4,6-Dichloro-2-methylthio-5-nitropyrimidine (5.25 g, 21.88 mmol) in methanol (40 mL) was treated with sodium methoxide (1.3 g, 24.06 mmol). The mixture was stirred at room temperature for 3 h. At this point the reaction was poured onto ice to give a brown solid which was filtered and washed with water. The solid was dried under vacuo to give 4-Chloro-6-methoxy-2-methylthio-5-nitropyrimidine (4.40 g, 85percent) as a brown solid. LRMS for C₆H₆Cl₁N₃O₃S (M+H)⁺ at m/z=235. The NMR spectrum obtained on the sample is compatible with its structure.

Reference： [1] Patent: US2007/270433, 2007, A1, . Location in patent: Page/Page column 51-52

3
[ 1979-97-1 ]
[ 1979-96-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	for 1 h; Heating / reflux	Step 2: A mixture 4,6-Dihydroxy-2-methylthio-5-nitropyrimidine (9.30 g, 45.81 mmol), phosphorus oxychloride (40 mL) and diethylaniline (12 mL) were refluxed for 1 hr. After partial evaporation the liquid was poured onto ice to give a brown solid which was filtered and washed with water. The solid was dried under vacuo to give 4,6-Dichloro-2-methylthio-5-nitropyrimidine (10.5 g, 95percent) as a brown solid. LRMS for C₅H₃C₁₂N₃O₂S (M+H)⁺ at m/z=240. The NMR spectrum obtained on the sample is compatible with its structure.
87%	at 20 - 105℃; for 1.25 h;	Step B: 4,6-Dichloro-2-methylsulfanyl-pyrimidin-5-ylamine. N,N-Diethylaniline (3.3 mL) was added dropwise to a stirred mixture of 2-methylsulfanyl-5-nitro-pyrimidine-4,6-diol (3.4 g, 17 mmol) and POCl₃ (15 mL) at rt. After 15 minutes (min), the reaction mixture was heated to 105° C. and stirred for 1 h. The cooled reaction mixture was poured onto ice (100 g) and then extracted with Et₂O (3*100 mL). The combined extracts were dried and concentrated, and the residue was purified directly by FCC to afford 4,6-dichloro-2-methylsulfanyl-5-nitro-pyrimidine as a colorless solid (3.5 g, 87percent).
87%	at 20 - 105℃; for 1.25 h;	Intermediate 2: 4,6-Dichloro-2-methylsulfanyl-pyrimidin-5-ylamine N,N-Diethylaniline (3.3 mL) was added dropwise to a stirred mixture of 2-methylsulfanyl-5-nitro-pyrimidine-4,6-diol (3.4 g, 17 mmol) and phosphoryl chloride (15 mL) at rt. After 15 min, the reaction mixture was heated to 105° C. for 1 h. The cooled reaction mixture was poured onto ice (100 g) and then extracted with Et₂O (3.x.100 mL). The combined extracts were dried, filtered, and concentrated. The residue was purified by FCC to afford a colorless solid (3.5 g, 87percent) as 4,6-dichloro-2-methylsulfanyl-5-nitro-pyrimidine.

78%	at 0 - 100℃;	N,N-dimethylaniline (76.7 mL, 0.61 mol) was added drop wise to POCI₃ (93.7 mL, 1.01 mol) at 0°C. G-2 (41 g, 201.79 mmol) was added portion wise at 0°C then the mixture was warmed to 100°C for 2h. The solution was concentrated under vacuum and the residual POCI₃ was removed by azeotropic evaporation with toluene (3 times). The resulting oil was taken up in a solution of CH₂CI₂-Heptane (70-30) and was filtered through a glass filter of Si0₂. The filtrate was concentrated and the residue was purified by preparative LC on (Irregular SiOH 20-45 ??? 1000 g DAVISIL), mobile phase (80percent Heptane, 20percent CH₂CI₂). The pure fractions were collected and concentrated to give 37.8 g (78percent yield) of intermediate H-2.
76%	With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline at 0 - 100℃; for 2 h;	Method VI: 4,6-Dichloro-2-methylthio-5-nitropyrimidine: A 500 mL round bottom flask was charged with POCl₃(89.5 mL, 0.960 mol, 5.00 equiv), and N,N-dimethylaniline (73.0 mL, 0.576 mol, 3.00 equiv). The reaction was cooled to 0° C., and 4,6-dihydroxy-2-methylthio-5-nitropyrimidine (39.0 g, 0.192 mol, 1.00 equiv) was added portionwise in a manner to control exotherm. Once the exotherm had subsided, the reaction was carefully warmed to 100° C. for 2 h. Reaction was then transferred to the upper reservoir of a continuous lower-density phase continuous extractor and extracted continuously with hot hexanes, which pooled in the lower reservoir. The lower reservoir was at 140° C. during extraction. After UV activity (254 nm) in the upper reservoir hexane phase was at its minimum, the system was cooled. The hexane phase was concentrated to an oil in vacuo. The residue was purified via silica gel chromatography (1 g residue/3 g silica) (Eluent: DCM). During loading (20 mL DCM was added to residue to aid fluidity) onto the column, there was a mild exotherm. After chromatography, crystalline 4,6-dichloro-2-methylthio-5-nitropyrimidine 34.9 g (76percent yield) was obtained. ¹H-NMR: 300 MHz, (CDCl₃) d (ppm): 2.62 (s, 3H). LCMS-ESI⁺: compound does not ionize.

Reference： [1] Patent: US2007/270433, 2007, A1, . Location in patent: Page/Page column 51
[2] Patent: US2008/4253, 2008, A1, . Location in patent: Page/Page column 13
[3] Patent: US2009/156599, 2009, A1, . Location in patent: Page/Page column 12
[4] Patent: WO2013/68438, 2013, A1, . Location in patent: Page/Page column 29-30
[5] Patent: US2010/143301, 2010, A1, . Location in patent: Page/Page column 45-46
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 6, p. 1658 - 1661
[7] Patent: WO2011/119518, 2011, A1, . Location in patent: Page/Page column 39; 81
[8] Synthetic Communications, 2018, vol. 48, # 6, p. 714 - 720
[9] Patent: WO2008/135785, 2008, A1, . Location in patent: Page/Page column 69

4
[ 1979-98-2 ]
[ 1979-96-0 ]

Reference： [1] Patent: WO2011/119518, 2011, A1,
[2] Patent: WO2013/68438, 2013, A1,

[ 1979-96-0 ] Synthesis Path-Downstream 1~88

1
[ 17356-08-0 ]
[ 1979-96-0 ]
[ 127726-63-0 ]

Reference： [1]Australian Journal of Chemistry,1990,vol. 43,p. 55 - 62

2
[ 1979-96-0 ]
[ 127726-61-8 ]

Reference： [1]Australian Journal of Chemistry,1990,vol. 43,p. 55 - 62

3
[ 1979-96-0 ]
[ 127726-62-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium peroxymonosulphate; tetrabutylammomium bromide; In water; acetone; at 20℃;	General procedure: A mixture of 2-(methylthio)pyrimidines (5 mmol), tetrabutylammonium bromide (0.16 g, 0.5 mmol, 10 mol%) and acetone (20 mL) was stirred at room temperature. The Oxone (12.5 mmol, 2.5 equiv) in water (20 mL) was added slowly to the vigorously stirred solution. After 4-6 h, TLC indicated the consumption of the starting material. The products 5 were isolated by filtering through a Buechner funnel and washed with water, and then dried to give the solid product. Yields, melting points and spectroscopic data for selected 2-(methylsulfonyl)pyrimidines are listed as follows.

Reference： [1]Synthetic Communications,2018,vol. 48,p. 714 - 720
[2]Australian Journal of Chemistry,1990,vol. 43,p. 55 - 62

4
[ 110-89-4 ]
[ 1445-45-0 ]
[ 75-64-9 ]
[ 109-73-9 ]
[ 1979-96-0 ]
butyl-(9-tert-butyl-8-methyl-2-piperidin-1-yl-9H-purin-6-yl)-amine [ No CAS ]