[ CAS No. 4425-56-3 ] {[proInfo.proName]}

Name: 4425-56-3|2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile|98%
Brand: Ambeed
SKU: A140484
Price: 5.0 USD
Availability: InStock
Rating: 96 (32 reviews)

,{[proInfo.pro_purity]}

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

2D 3D

Structure of 4425-56-3 * 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 [ 4425-56-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4425-56-3 ]

SDS Specification

Alternatived Products of [ 4425-56-3 ]

Product Details of [ 4425-56-3 ]

CAS No. :	4425-56-3	MDL No. :	MFCD00051958
Formula :	C₅H₃N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HAUXRJCZDHHADG-UHFFFAOYSA-N
M.W :	137.10	Pubchem ID :	78145
Synonyms :

Calculated chemistry of [ 4425-56-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	32.4
TPSA :	89.51 Å²

Pharmacokinetics

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) :	-7.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.12
Log Po/w (XLOGP3) :	-0.93
Log Po/w (WLOGP) :	-1.07
Log Po/w (MLOGP) :	-1.71
Log Po/w (SILICOS-IT) :	1.2
Consensus Log Po/w :	-0.48

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.55
Solubility :	38.8 mg/ml ; 0.283 mol/l
Class :	Very soluble
Log S (Ali) :	-0.47
Solubility :	46.9 mg/ml ; 0.342 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.52
Solubility :	4.11 mg/ml ; 0.03 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 4425-56-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4425-56-3 ]

* 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 [ 4425-56-3 ]
Downstream synthetic route of [ 4425-56-3 ]

[ 4425-56-3 ] Synthesis Path-Upstream 1~6

1
[ 1187-34-4 ]
[ 4425-56-3 ]

Reference： [1] Patent: US2006/25433, 2006, A1, . Location in patent: Page/Page column 104

2
[ 85690-57-9 ]
[ 4425-56-3 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1994, vol. 59, # 8, p. 1841 - 1852

3
[ 162129-62-6 ]
[ 4425-56-3 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1994, vol. 59, # 8, p. 1841 - 1852

4
[ 1187-34-4 ]
[ 4425-56-3 ]

Reference： [1] Journal of the Chemical Society, 1955, p. 1834,1838

5
[ 4425-56-3 ]
[ 23945-44-0 ]

Reference： [1] Journal of the Chemical Society, 1955, p. 1834,1838

6
[ 4425-56-3 ]
[ 3177-24-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 16, p. 6129 - 6152
[2] Patent: US2006/25433, 2006, A1, . Location in patent: Page/Page column 104

[ 4425-56-3 ] Synthesis Path-Downstream 1~37

1
[ 4425-56-3 ]
[ 23945-44-0 ]

Reference： [1]Journal of the Chemical Society,1955,p. 1834,1838

2
[ 1187-34-4 ]
[ 4425-56-3 ]

Reference： [1]Journal of the Chemical Society,1955,p. 1834,1838

3
[ 85690-57-9 ]
[ 4425-56-3 ]
5-methoxycarbonylcytosine [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1994,vol. 59,p. 1841 - 1852

4
[ 64-19-7 ]
[ 4425-56-3 ]
[ 82318-55-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 887 - 898

5
[ 4425-56-3 ]
[ 51-21-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3181 - 3190

6
[ 4425-56-3 ]
[ 65906-21-0 ]

Yield	Reaction Conditions	Operation in experiment
	With fluorine; In water;	EXAMPLE 21 In 150 ml. of water is suspended 2.05 g. of <strong>[4425-56-3]1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile</strong> and, with vigorous stirring, fluorine gas previously diluted with 3 times its volume of nitrogen gas is introduced (reaction mixture 26-29 C.). When about 4.5 molar equivalents of fluorine has been introduced (over about 5 hours), the reaction mixture is concentrated to dryness and the residue is chromatographed on a column of silica gel (solvent:chloroform-methanol=13:1) to give 1.86 g. of 5-fluoro-6-hydroxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carbonitrile as a white crystalline powder. Melting Point: 158-160 C.(decomp.). NMR spectrum (DMSO-d6) delta: 5.35(1H, m), 7.75(1H, broad), 9.00(1H, broad), 11.40(1H, broad). Elemental analysis, for C5 H4 FN3 O3: Calcd.: C, 34.69; H, 2.33; N, 24.27. Found: C, 34.39; H, 2.27; N, 24.16.

Reference： [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3181 - 3190
[2]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 887 - 898
[3]Patent: US4329460,1982,A

7
[ 4425-56-3 ]
[ 65906-21-0 ]
[ 65906-22-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3181 - 3190

8
[ 162129-62-6 ]
[ 4425-56-3 ]
5-carboxycytosine [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1994,vol. 59,p. 1841 - 1852

9
[ 169736-17-8 ]
[ 4425-56-3 ]
C₂₆H₂₃N₃O₆S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 789 - 795

Yield	Reaction Conditions	Operation in experiment
		Particularly preferred inactivators of uracil reductase for use in accordance with the invention are 5-ethynyluracil and 5-propynyluracil. Other inactivators for such use include: 5-ethynyluracil 5-cyanouracil 5-propynyluracil 5-bromoethynyluracil 5-(1-chlorovinyl)uracil 5-iodouracil ...
		Particularly preferred inactivators of uracil reductase for use in accordance with the invention are 5-ethynyluracil and 5-propynyluracil. other inactivators for such use include:- 5-cyanouracil 5-bromoethynyluracil 5-(l-chlorovinyl)uracil 5-iodouracil 5-hex-1-ynyluracil 5-vinyluracil 5-trifluoromethyluracil 5-bromouracil
		Particularly preferred uracil derivatives which form part of the compounds as hereinbefore defined are 5-ethynyluracil and 5-propynyluracil. Other such inactivators include: 5-cyanouracil 5-bromoethynyluracil 5-(1-chlorovinyl) uracil 5-iodouracil 5-hex-1-ynyluracil 5-vinyluracil 5-trifluoromethyluracil 5-bromouracil

12
β-<S-ethyl-isothioureido>-α-cyano-acrylic acid-<S-ethyl-isothio ureide> [ No CAS ]
[ 4425-56-3 ]

Reference： [1]American Chemical Journal,1909,vol. 42,p. 506,510, 512

13
4-oxy-2-ethylsulfanyl-pyrimidine-carboxylic acid-⁽⁵⁾-nitrile [ No CAS ]
[ 4425-56-3 ]

Reference： [1]American Chemical Journal,1909,vol. 42,p. 506,510, 512

14
[ 7647-01-0 ]
[ 4425-56-3 ]
[ 66-22-8 ]

Reference： [1]American Chemical Journal,1909,vol. 42,p. 506,510, 512

15
[ 70-34-8 ]
[ 4425-56-3 ]
1-(2,4-dinitro-phenyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4653 - 4657

16
[ 4425-56-3 ]
[ 65906-82-3 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; In ethanol; acetic acid;	EXAMPLE 78 In 400 ml. of acetic acid is suspended 2.05 g. of <strong>[4425-56-3]1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile</strong> and, with vigorous stirring a mixed gas of fluorine and nitrogen (15:85 (V/V)) is introduced. When about 1.5 molar equivalents to fluorine to the substrate has been introduced, the reaction mixture is evapolated to dryness. Ethanol (70 ml.) is added to the residue and the mixture is heated under reflux for 2 hours and, then, evapolated to dryness again. The resultant syrup is subjected to column chromatography on silica gel (solvent:benzene-acetone=4:1(V/V)) to recover 1.54 g. of 5-fluoro-6-ethoxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carbonitrile as white crystals. Melting Point: 195-196 C. NMR spectrum (DMSO-d6) delta: 1.07(3H, t, J=7HZ), 3.64(2H, qd, J=7HZ and J=2HZ), 5.42(1H, dd, J=4HZ and J=2HZ), 9.38(1H, broad), 11.59(1H, broad). Elemental analysis, for C7 H8 FN3 O3: Calcd.: C, 41.80; H, 4.01; N, 20.89. Found: C, 41.44; H, 3.95; N, 20.70.

Reference： [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 887 - 898
[2]Patent: US4329460,1982,A

17
[ 6940-78-9 ]
[ 4425-56-3 ]
[ 762302-92-1 ]

Yield	Reaction Conditions	Operation in experiment
		Zu einer Loesung von 2, 06 g (15, 0 MMOL) 5-Cyanouracil in 50 mi Dimethylsulfoxid (DMSO) und 20, 0 ml N, N-Dimethylformamid (DMF) tropfte man bei 0 C 2, 6 g (15, 0 MMOL) 1-Brom-4-chlorbutan und gab 2, 07 g (15, 0 MMOL) K2CO3 portionsweise ueber 1 Stunde zu. Danach ruehrte man das Gemisch 10 Minuten bei 20C (dialkyliertes Produkt schon erkennbar). Zu dem Reaktionsgemisch gab man Wasser und extrahierte danach die waessrige Mischung zweimal mit Diethylether und zweimal mit Methylenchlorid. Man stellte die waessrige Phase auf pH 3-4 und extrahierte anschliessend mit Methylenchlo- rid. Danach trocknete man die Methylenchlorid-Phase, filtrierte das Trockenmittel ab und engte das Loesungsmittel bis zur Trockne im Vakuum ; Ausbeute : 0, 6 G. 1- (4- Chlorbutyl)-2, 4-DIOXO-1, 2, 3, 4-TETRAHYDROPYRIMIDIN-5-CARBONITRIL wurde ohne weitere Rei- nigung im naechsten Schritt eingesetzt. ESI-MS : [M+H+] = 228, 05.

Reference： [1]Patent: WO2004/80981,2004,A1 .Location in patent: Page 62

18
[ 4425-56-3 ]
[ 3177-24-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-diethylaniline; trichlorophosphate; at 25 - 115℃; for 3h;	To a mixture of the above uracil (15.41 g, 112.5 mmol) and phosphorus oxychloride (157.4 mL, 1.69 mol) was added N,N-diethylaniline (34.2 mL, 225 mmol), cautiously, at 25 C. The reaction was then heated at 115 C. for 3 h after which the mixture was cooled to 40 C. and concentrated in vacuo to remove excess POCl3. The remaining liquid was poured slowly onto ice-water with rapid stirring and the precipitated product was filtered. The aqueous layer was then extracted with chloroform and the extract was washed with 1 N HCl before concentrating in vacuo. This material was combined with the previously filtered material to afford 2,4-dichloro-pyrimidine-5-carbonitrile (15.36 g, 79%).

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 6129 - 6152
[2]Patent: US2006/25433,2006,A1 .Location in patent: Page/Page column 104

19
[ 1187-34-4 ]
[ 4425-56-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 10 4-[(trans-4-aminocyclohexyl)methyl]amino}-2-[2-(trifluoromethoxy)-benzyl]amino}pyrimidine-5-carbonitrile To a mixture of N-cyanoacetylurethane (100 g, 640.5 mmol) in acetic anhydride (160 mL) was added triethyl orthoformate (26.6 mL, 160 mmol). The mixture was stirred at reflux for 2.5 h; it was then cooled to 25 C. whereupon crystals formed. The reaction mixture was filtered and the collected solid was washed with hexanes and dried under vacuum to afford 21.4 g (67%) of the desired product. Ammonium hydroxide (150 mL) was added to the above acrylamide (54.5 g, 258.29 mmol) in H2O (150 mL) at 25 C. followed by NaOH (32 g) in H2O (150 mL) dropwise over 10 min. The mixture was then heated at 70 C. with stirring for 1 h and then cooled to 25 C. The reaction mixture was filtered while basic, and then acidified to pH 4 with HCl and filtered to yield 25.4 g of uracil.

Reference： [1]Patent: US2006/25433,2006,A1 .Location in patent: Page/Page column 104

20
[ 4425-56-3 ]
[ 468067-75-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; triethylamine; In methanol;	Preparation 1 N'-Hydroxy-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinecarboximidamide <strong>[4425-56-3]5-Cyano uracil</strong> (2.0 g, 14.6 mmol) was suspended in methanol (50 mL), then hydroxylamine hydrochloride (1.4 g, 20.0 mmol) and triethylamine (2.8 mL, 20.0 mmol) were added and the mixture was heated to reflux overnight. The mixture was cooled to room temperature, the solid was collected by filtration, washed with methanol and dried to give the title compound as a pale yellow solid (1.8 g). 1H NMR (400 MHz, D6-DMSO) delta 5.71 (br s, 2H), 7.62 s, 1H), 11.0-11.4 (br s, 1H). LRMS (ES) 363 (2M+Na), 193 (M+Na), 171 (M+H).

Reference： [1]Patent: US2003/69291,2003,A1

21
[Ru(2-2'-bipyridine)2(triflate)2] [ No CAS ]
[ 4425-56-3 ]
[Ru(2-2'-bipyridine)2(5-cyanouracil)2]⁽²⁺⁾ [ No CAS ]

Reference： [1]Inorganic Chemistry,2011,vol. 50,p. 9213 - 9215

22
[ 22353-96-4 ]
[ 4425-56-3 ]
[ 1350660-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h;	General procedure: To a solution of oxime 1a-i (0.4 mmol) in dry DMF (3 ml), NCS (0.44 mmol, 0.059 g) was added at room temperature while stirring. Completion of the reaction was indicated by TLC (EtOAc/n-hexane, 1:1 v/v). The solution of generated oximoyl chloride 2a-i was immediately used for the next step without purification. 5-Cyanouracil (3) (0.35 mmol, 0.048 g) was added followed by dropwise addition of Et3N (0.4 mmol, 0.06 ml). In the case of 1h, 0.8 mmol of Et3N was used. The reaction mixture was stirred for 24 h at room temperature. After that time the solvent was removed under reduced pressure and the residue purified on a silica gel packed column using EtOAc/n-hexane (1:1) as eluent.