[ CAS No. 1187-34-4 ] {[proInfo.proName]}

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Quality Control of [ 1187-34-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1187-34-4 ]

SDS Specification

Alternatived Products of [ 1187-34-4 ]

Product Details of [ 1187-34-4 ]

CAS No. :	1187-34-4	MDL No. :	MFCD00114882
Formula :	C₉H₁₂N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	212.20	Pubchem ID :	-
Synonyms :

Safety of [ 1187-34-4 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Application In Synthesis of [ 1187-34-4 ]

* 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 [ 1187-34-4 ]
Downstream synthetic route of [ 1187-34-4 ]

[ 1187-34-4 ] Synthesis Path-Upstream 1~3

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

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

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

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

3
[ 1187-34-4 ]
[ 23945-44-0 ]

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

[ 1187-34-4 ] Synthesis Path-Downstream 1~17

1
[ 6629-04-5 ]
[ 108-24-7 ]
[ 1187-34-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With orthoformic acid triethyl ester; for 2.5h;Heating / reflux;	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.

Reference： [1]Patent: US2006/25433,2006,A1 .Location in patent: Page/Page column 103
[2]Journal of the Chemical Society,1955,p. 1834,1838

2
[ 141-43-5 ]
[ 1187-34-4 ]
[ 98279-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	With water

Reference： [1]Shaw; Warrener [Journal of the Chemical Society, 1959, p. 50,53]

3
[ 75-31-0 ]
[ 1187-34-4 ]
[ 57712-59-1 ]

Yield	Reaction Conditions	Operation in experiment
	With water

Reference： [1]Atkinson et al. [Journal of the Chemical Society, 1956, p. 4118,4120]

4
[ 56-40-6 ]
[ 1187-34-4 ]
[ 56673-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide

Reference： [1]Atkinson et al. [Journal of the Chemical Society, 1956, p. 4118,4120]

5
[ 74-89-5 ]
[ 1187-34-4 ]
[ 7465-66-9 ]

Yield	Reaction Conditions	Operation in experiment
	With water

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

6
[ 100-46-9 ]
[ 1187-34-4 ]
[ 57712-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With water

Reference： [1]Atkinson et al. [Journal of the Chemical Society, 1956, p. 4118,4120]

7
[ 1187-34-4 ]
[ 4425-56-3 ]

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

8
[ 6629-04-5 ]
[ 122-51-0 ]
[ 1187-34-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 1380 - 1388

9
[ 6629-04-5 ]
[ 122-51-0 ]
[ 1187-34-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404
[2]Journal of Physical Organic Chemistry,2005,vol. 18,p. 1183 - 1189

11
[ 41365-75-7 ]
[ 1187-34-4 ]
[ 952402-34-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	In water; at 80℃; for 0.166667h;	Preparation 34 : 1-(3,3-Diethoxy-propyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5- carbonitrile (Prep34); <n="82"/>(2-Cyano-3-ethoxy-acryloyl)-carbamic acid ethyl ester (Prep 33, 300 mg, 1.42 mmol) was suspended in water (20 ml_); 3,3-diethoxypropylamine (460 mul, 2.84 mmol) was added and the mixture warmed at 800C for 10 minutes. The reaction mixture was lyophilized and the residue was purified by flash chromatography with petroleum ether-ethyl acetate (1-1 ) to give 350 mg of the title compound (91% yield) MS (ES) (mlz): 268.3 [M+H]+.1H-NMR (DMSO-Cl6) delta:11.93 (br. s., 1 H), 8.63 (s, 1 H), 4.55 (t, 1 H), 3.79 (t, 2 H), 3.49 - 3.60 (m, 2 H), 3.35 - 3.46 (m, 2 H), 1.86 - 1.99 (m, 2 H), 1.09 (t, 6 H).

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 79-80

12
[ 1187-34-4 ]
[ 23945-44-0 ]

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

13
[ 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

14
[ 1187-34-4 ]
[ 56-40-6 ]
5-cyano-2,4-dioxo-1-pyrimidinylacetic acid [ No CAS ]
[ 56673-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	In sodium hydroxide	2 2-(5-Cyano-2,4-dioxo-1-pyrimidinyl)acetic acid EXAMPLE 2 2-(5-Cyano-2,4-dioxo-1-pyrimidinyl)acetic acid The compound α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide (21.2 g, 0.1 mole), prepared in accordance with the procedure of M. R. Atkinson, G. Shaw and R. N. Warrener, J. Chem. Soc., 4118 (1956), is added in portions to a solution of glycine (7.5 g, 0.1 mole) dissolved in 2 Normal sodium hydroxide (50 ml). After solution is achieved, 8 ml of a 50% sodium hydroxide solution is added, the mixture is stirred for a period of 18 hours, chilled, acidified and filtered to give 6 g of 5-cyano-2,4-dioxo-1-pyrimidinylacetic acid having a m.p. of 265°C.

Reference： [1]Current Patent Assignee: SANOFI - US3956288, 1976, A

15
[ 53439-88-6 ]
[ 1187-34-4 ]
1-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	In N,N-dimethyl-formamide; acetonitrile;Reflux;	A mixture of 1.00 g (4.71 mmol) of ethyl (2-cyano-3-ethoxyprop-2-enoyl)carbamate (for preparation see: Senda, Shigeo, Hirota, Kosaku, Notani, Jiyoji; Chemical & Pharmaceutical Bulletin (1972), 20(7), 1380-8) and 835 mg (4.71 mmol) of <strong>[53439-88-6]5-amino-1,3-dimethyl-1,3-dihydro-2H-benzimidazol-2-one</strong> in 5 ml of acetonitrile and 10 ml of DMF was stirred at reflux temperature overnight. After cooling to RT, the mixture was diluted with 150 ml of diethyl ether and the precipitate was filtered off. The filter residue was stirred with 10 ml of methanol, and the solid was filtered off, washed with a little methanol and ether and dried under high vacuum. This gave 703 mg (45% of theory) of the title compound. LC-MS (Method 1): Rt=0.53 min; m/z=298 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=3.30 (br. s, 3H), 3.36 (br. s, 3H), 7.17 (dd, 1H), 7.23-7.28 (m, 1H), 7.34 (d, 1H), 8.77 (s, 1H).

Reference： [1]Patent: US2016/244415,2016,A1 .Location in patent: Paragraph 0723; 0724; 0725; 0726

16
[ 99584-10-8 ]
[ 1187-34-4 ]
1-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	Stage #1: 6-amino-3-methyl-1,3-benzoxazol-2(3H)-one; α-Cyano-β-ethoxy-N-(ethoxycarbonyl)acrylamide With triethylamine In N,N-dimethyl-formamide; acetonitrile Reflux; Stage #2: In N,N-dimethyl-formamide at 80℃; for 4h;	31A 1-(3-Methyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile A mixture of 1.00 g (4.71 mmol) of ethyl (2-cyano-3-ethoxyprop-2-enoyl)carbamate and 774 mg (4.71 mmol) of 6-amino-3-methyl-1,3-benzoxazol-2(3H)-one in 10 ml of acetonitrile and 10 ml of DMF was stirred at reflux temperature overnight. After cooling to RT, the solid was filtered off, washed with acetonitrile and dried under HV. This solid was taken up in 20 ml of DMF, 985 μl (7.07 mmol) of triethylamine were added and the solution was stirred at 80° C. for 4 h. After cooling to RT, the mixture was diluted with 200 ml of water. The solid was filtered off and washed with water. The entire filtrate was allowed to stand at 20° C. overnight, once again resulting in the precipitation of a solid. The solid was filtered off and dried under high vacuum. This gave 276 mg (19% of theory) of the title compound. LC-MS (Method 19): Rt=1.21 min; m/z=285 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=3.38 (s, 3H), 7.34-7.40 (m, 2H), 7.56 (d, 1H), 8.78 (s, 1H), 12.14 (br. s, 1H).

Reference： [1]Current Patent Assignee: BAYER AG - US2016/244415, 2016, A1 Location in patent: Paragraph 0727; 0728; 0729; 0730

17
[ 920509-28-0 ]
[ 1187-34-4 ]
1-(3,5-dichloro-4-((5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)phenyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1%	In N,N-dimethyl-formamide at 100 - 130℃; for 1.5h; Microwave irradiation;	12.5 Step 5: Example 12 Example 012e (313 mg, 1.0 mmol) and Example 12g (255 mg, 1.2 mmol) were dissolved in DMF (4 mL). The mixture was irradiated in a microwave reactor at l00°C for 1 h and l30°C for 30 min. The mixture was filtered to remove all solids and partitioned. The aqueous layer was extracted with DCM (10 mL3) and the combined organic layer was washed with brine, and dried over sodium sulphate. The crude residue was purified by prep-HPLC (by Ultimate XB-C18, 50250 mm, 10 pm, Mobile Phase: A (H20)/B (MeCN); Range of ratio: A/B (80%/20%) to A/B (60%/40%) 10 min and to A/B (40%/60%) 35 min, V = 80 mL/min, wavelength 214 nm) to afford Example 12 (2.8 mg, yield 1%). LCMS [M+l]+= 435.2. *HNMR (400 MHz, DMSO-ri6) d 12.24 (s, 1H), 8.76 (s, 1H), 7.83 (s, 2H), 7.44 (0792) (s, 1H), 3.07-3.03 (m, 1H), 1.20 (d, J= 6.8 Hz, 6H).

Reference： [1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - WO2019/240938, 2019, A1 Location in patent: Paragraph 00311; 00315

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[ CAS No. 1187-34-4 ] {[proInfo.proName]}

Quality Control of [ 1187-34-4 ]

Related Doc. of [ 1187-34-4 ]

Product Details of [ 1187-34-4 ]

Safety of [ 1187-34-4 ]

Application In Synthesis of [ 1187-34-4 ]

[ 1187-34-4 ] Synthesis Path-Upstream 1~3

[ 1187-34-4 ] Synthesis Path-Downstream 1~17

Precautionary Statements-General

Prevention

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