[ CAS No. 18465-11-7 ] {[proInfo.proName]}

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Quality Control of [ 18465-11-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 18465-11-7 ]

CAS No. :	18465-11-7	MDL No. :	MFCD06761742
Formula :	C₈H₁₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	134.18	Pubchem ID :	-
Synonyms :

Safety of [ 18465-11-7 ]

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Application In Synthesis of [ 18465-11-7 ]

* 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.

Downstream synthetic route of [ 18465-11-7 ]

[ 18465-11-7 ] Synthesis Path-Downstream 1~13

1
[ 617-36-7 ]
[ 18465-11-7 ]
[ 46297-10-3 ]

Reference： [1]Journal of the Indian Chemical Society,1926,vol. 3,p. 402
Chemisches Zentralblatt,1927,vol. 98,p. 1470

2
[ 18465-11-7 ]
[ 77-25-8 ]
5,5-diethyl-2-<i>p</i>-tolyl-1<i>H</i>-pyrimidine-4,6-dione [ No CAS ]

Reference： [1]Patent: DE520854,1928,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 17,p. 2614

3
[ 33844-21-2 ]
[ 18465-11-7 ]
[ 1224442-37-8 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 1887 - 1890

4
[ 127956-11-0 ]
[ 18465-11-7 ]
[ 1450790-51-8 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6495 - 6511

5
[ 13959-02-9 ]
[ 18465-11-7 ]
[ 1613435-84-9 ]

Yield	Reaction Conditions	Operation in experiment
9%	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 20 - 80℃; for 13h;Inert atmosphere;	2-(4-Methylphenyl)pyrido[3,4-djpyrimidin-4-one (41b). 3-Bromopyridine-3-carboxylic acid 4093 (101.5 mg, 0.50 mmol) was stirred with 4-methylbenzimidamide 48b (67 mg, 0.50 mmol), copper(l) iodide (19 mg, 0.10 mmol) and caesium carbonate (325 mg, 1.0 mmol) in dimethylformamide (5 mL) at 80C for 3 h, then at room temperature for 10 h under argon. The mixture was cooled and filtered and the solvent was evaporated. The residue was dissolved in methanol, the precipitate was filtered and the solvent was evaporated from the filtrate. The residue was dissolved in saturated aqueous ethylenediaminetetraacetic acid (20 mL) and this solution was extracted with dichloromethane (3 chi 25 mL). The combined extracts were dried (magnesium sulfate) and the solvent was evaporated to give 2-(4-methylphenyl)pyrido[3,4-cf]pyrimidin-4-one 41 b (10 mg, 9%) as a white powder: mp 214-216C, 1H NMR ((CD3)2SO) delta 2.44 (3 H, s, Me), 7.36 (2 H, d, J = 8.1 Hz, Ph 3,5-H2), 7.91 (1 H, d, J = 5.2 Hz, 5-H), 8.24 (2 H, d, J = 8.2 Hz, Ph 2,6-H2), 8.52 (1 H, d, J = 5.2 Hz, 6-H), 9.03 (1 H, s, 7-H), 10.20 (1 H, br, NH); 13C NMR ((CD3)2SO) (HSQC / HMBC) delta 20.97 (Me), 1 18.16 (5-C), 126.00 (4a-C), 127.47 (Ph 1-C), 127.47 (Ph 2,6-C2), 128.85 (Ph 3,5-C2), 129.45 (Ph 4-C), 144.00 (6- C), 149.00 (8a-C), 150.40 (8-C), 168.90 (2-C); MS m/z 236.0836 (M - HV (C14H10N3O requires 236.0824).

Reference： [1]Patent: WO2014/87165,2014,A1 .Location in patent: Page/Page column 97-98

6
[ 15366-62-8 ]
[ 18465-11-7 ]
[ 16952-49-1 ]

Yield	Reaction Conditions	Operation in experiment
42%	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 12h;Inert atmosphere;	2-(4-Methylphenyl)pyrido[4,3-d]pyrimidin-4-one (43b). 4-Bromopyridine-3-carboxylic acid (101.5 mg, 0.5 mmol) was stirred with 4-methylbenzimidamide (67 mg, 0.5 mmol), copper(l) iodide (19.2 mmol, 0.1 mmol) and caesium carbonate (325 mg, 1.0 mmol) in dimethylformamide (5 mL) at 80C for 12 h under argon. The mixture was filtered and the solvent was evaporated. The residue was suspended in methanol. The mixture was filtered and the solvent was evaporated from the filtrate. The evaporation residue was dissolved in aqueous ethylenediaminetetraacetic acid (saturated, 20 mL). The solution was extracted with ethyl acetate (6 chi 25 mL). The combined organic extracts were dried (magnesium sulfate) and the solvent was evaporated to give 2-(4- methylphenyl)pyrido[4,3-d]pyrimidin-4-one 43b (46 mg, 42%) as an ivory-coloured powder: mp 276-278C (lit.72 296-299C); 1H NMR ((CD3)2SO) delta 2.45 (3 H, s, Me), 7.29 (2 H, d, J = 8.0 Hz, Ph 3,5-H2), 7.64 (1 H, d, J = 5.4 Hz, 5-H), 8.18 (2 H, d, J = 8.2 Hz, Ph 2,6-H2), 8.85 (1 H, br, 6-H), 9.33 (1 H, br, 8-H); 13C NMR ((CD3)2SO) (HSQC / HMBC) delta 21.0 (Me), 120.12 (8a-C), 120.39 (5-C), 128.17 (Ph 2,6-C2), 129.21 (Ph 3,5- C2), 129.82 (Ph 1-C), 131.48 (Ph 4-C), 142.27 (3-C), 149.45 (8-C), 157.37 (4a-C), 162.37 (1-C); MS m/z 238.0975 (M + H)+ (C14H12N30 requires 238.0984).

Reference： [1]Patent: WO2014/87165,2014,A1 .Location in patent: Page/Page column 99

7
[ 15366-62-8 ]
[ 18465-11-7 ]
2-(4-methylphenyl)pyrido[4,3-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 12h;Inert atmosphere;	Compound 37 (101.5 mg, 0.5 mmol) was stirred with 45b(67 mg, 0.5 mmol), CuI (19.2 mmol, 0.1 mmol) and Cs2CO3(325 mg, 1.0 mmol) in DMF (5 mL) at 80 C for 12 h under Ar.The mixture was filtered. The evaporation residue was suspendedin MeOH and filtered. The evaporation residue, in sat. aq EDTA(20 mL), was extracted with EtOAc (6). Drying and evaporationgave 16b (46 mg, 42%) as an off-white powder: mp 276-278 C(lit.51 296-299 C); 1H NMR d 2.45 (3H, s, Me), 7.29 (2H, d,J = 8.0 Hz, Ph 3,5-H2), 7.64 (1H, d, J = 5.4 Hz, 5-H), 8.18 (2H, d,J = 8.2 Hz, Ph 2,6-H2), 8.85 (1H, br, 6-H), 9.33 (1H, br, 8-H); 13CNMR d 21.0 (Me), 120.12 (8a-C), 120.39 (5-C), 128.17 (Ph 2,6-C2),129.21 (Ph 3,5-C2), 129.82 (Ph 1-C), 131.48 (Ph 4-C), 142.27 (3-C), 149.45 (8-C), 157.37 (4a-C), 162.37 (1-C); MS m/z 238.0984(M+H)+ (C14H12N3O requires 238.0980).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3013 - 3032

8
[ 13959-02-9 ]
[ 18465-11-7 ]
2-(4-methylphenyl)pyrido[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 20 - 80℃; for 15h;Inert atmosphere;	Compound 31 (101.5 mg, 0.50 mmol) was stirred with 45b(67 mg, 0.50 mmol), CuI (19 mg, 0.10 mmol) and Cs2CO3 (325 mg,1.0 mmol) in DMF (5 mL) at 80 C for 3 h, then at 20 C for 12 hunder Ar. The evaporation residue, in MeOH, was filtered. Theevaporation residue, in sat. aq EDTA (20 mL), was extracted thricewith CH2Cl2. Drying and evaporation gave 15b (10 mg, 9%) as awhite powder: mp 214-216 C, 1H NMR d 2.44 (3H, s, Me), 7.36(2H, d, J = 8.1 Hz, Ph 3,5-H2), 7.91 (1H, d, J = 5.2 Hz, 5-H), 8.24(2H, d, J = 8.2 Hz, Ph 2,6-H2), 8.52 (1H, d, J = 5.2 Hz, 6-H), 9.03(1H, s, 7-H), 10.20 (1H, br, NH); 13C NMR d 20.97 (Me), 118.16(5-C), 126.00 (4a-C), 127.47 (Ph 1-C), 127.47 (Ph 2,6-C2), 128.85(Ph 3,5-C2), 129.45 (Ph 4-C), 144.00 (6-C), 149.00 (8a-C), 150.40(8-C), 168.90 (2-C); MS m/z 236.0836 (M - H)- (C14H10N3O requires236.0824).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3013 - 3032

9
[ 57611-47-9 ]
[ 18465-11-7 ]
6-benzyl-2-(4-methylphenyl)-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium methylate; In methanol; for 10h;Reflux;	General procedure: Compound 46 (1.42 g, 5.0 mmol) was boiled under reflux with45a (600 mg, 5.0 mmol) and NaOMe (from Na (690 mg, 30 mmol))in dry MeOH (30 mL) for 10 h, then cooled. The evaporation residue,in water, was sonicated for 5 min. The suspension was keptat 2-8 C for 1 h. The solid was collected, washed (water, EtOAc)and dried to give 47a (840 mg, 53%) as an off-white powder.

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3013 - 3032

10
[ 57611-47-9 ]
[ 18465-11-7 ]
2-(4-methylphenyl)-4-oxo-3,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidin formate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3013 - 3032

11
[ 18465-11-7 ]
[ 1655-07-8 ]
2-(p-tolyl)-5,6,7,8-tetrahydroquinazolin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.2%	With potassium <i>tert</i>-butylate In methanol at 0℃; for 4.5h; Reflux;	2-Phenyl-5,6,7,8-tetrahydroquinazolin-4-ol(8b) General procedure: To a suspension of benzimidamide hydrochloride (7, 50 mmol) and ethyl2-oxocyclohexanecarboxylate (55 mmol) in MeOH (200 mL) was added t-BuOK (10 mmol) portionwise, withstirring at 0 °C for 30min. The resulting mixture was heat to reflux for 4h andthen cool down to room temperature. After that, ice water (200mL) was added andneutralized with citric acid. The precipitate thus formed was filtered andwashed with water. The crude residue obtained was recrystallized from i-PrOH to give2-phenyl-5,6,7,8-tetrahydroquinazolin-4-ol, 8b, as a white solid (8.9g, 78.7%), m.p. 246 - 249 °C.

Reference： [1]Lan, Yu; Songyang, Yiyan; Zhang, Lingli; Peng, Yan; Song, Jinchun [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 2051 - 2056]

12
[ 10340-91-7 ]
[ 18465-11-7 ]
[ 22265-37-8 ]
2-(4-methoxyphenyl)-4-(p-tolyl)-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With silver hexafluoroantimonate In toluene at 140℃; for 10h; Schlenk technique; Inert atmosphere;	General procedure for synthesis of unsymmetrical 2,4-diaryl-1,3,5-triazines General procedure: In a Schlenk tube, the mixture of aryl amidine 1 (0.2 mmol), amidine 1’ (0.2 mmol), AgSbF6 (0.015 mmol) and benzyl isocyanide 2 (0.3 mmol) were stirred in toluene (2mL) at 140°C for 10 h. The solvent was removed under vacuum. The residue was directly purified by flash chromatography (eluent: 10:1 petroleum ether/ethyl acetate) to give the desired unsymmetrical 2,4-diaryl-1,3,5-triazine.

Reference： [1]Lu, Xiaodong; Xin, Xiaoyi; Wan, Boshun [Tetrahedron Letters, 2018, vol. 59, # 4, p. 361 - 364]

13
[ 6326-27-8 ]
[ 18465-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In water at 20℃; for 1h;	General procedure for synthesis of aryl amidines General procedure: A 100 mL flask was charged with 30 mL of anhydrous MeOH, 10 mmol of the arylnitrile, and 1.0 mmol of sodium methoxide. The complex was protected from moisture and stirred for 48 h. Then, 10 mmol of NH4Cl was added and stirring was continued for 24 h. Unreacted NH4Cl was filtered, and methanol was stripped from the filtrate to afford the product aryl amidine hydrochlorides, which was dissolved in 2.5 mL 8M sodium hydroxide aqueous solution and stirred for 1 h. Then chloroform (20 ml x 3) and H2O (20 ml x 3) were added successively to extract the product, and the combined organic layer was dried with anhydrous MgSO4 and then evaporated under vacuum to remove the organic solvent to give the desired arylamidine.

Reference： [1]Lu, Xiaodong; Xin, Xiaoyi; Wan, Boshun [Tetrahedron Letters, 2018, vol. 59, # 4, p. 361 - 364]

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[ CAS No. 18465-11-7 ] {[proInfo.proName]}

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[ 18465-11-7 ] Synthesis Path-Downstream 1~13

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