1920-66-7|4-Amino-2-chloro-5-nitropyrimidine| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 1920-66-7 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 1920-66-7 ]

CAS No. :	1920-66-7
Formula :	C₄H₃ClN₄O₂
M.W :	174.55
SMILES Code :	NC1=NC(Cl)=NC=C1[N+]([O-])=O
MDL No. :	MFCD00127771
InChI Key :	RZGOEIWDMVQJBQ-UHFFFAOYSA-N
Pubchem ID :	74716

Safety of [ 1920-66-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1920-66-7 ]

* 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 [ 1920-66-7 ]

[ 1920-66-7 ] Synthesis Path-Downstream 1~35

1
[ 110-86-1 ]
[ 1920-66-7 ]
1-(4-amino-5-nitro-pyrimidin-2-yl)-pyridinium; chloride [ No CAS ]

References: [1]Journal of the Chemical Society,1955,p. 4354,4357.

2
[ 504-29-0 ]
[ 1920-66-7 ]
5-nitro-<i>N</i>²-[2]pyridyl-pyrimidine-2,4-diyldiamine [ No CAS ]

References: [1]Journal of the Chemical Society,1955,p. 4354,4357.

3
[ 504-29-0 ]
[ 1920-66-7 ]
2-amino-1-(4-amino-5-nitro-pyrimidin-2-yl)-pyridinium; chloride [ No CAS ]

References: [1]Journal of the Chemical Society,1955,p. 4354,4357.

4
[ 1920-66-7 ]
[ 74-93-1 ]
[ 84928-85-8 ]

References: [1]Journal of the Chemical Society,1954,p. 2060,2062.

5
[ 1920-66-7 ]
[ 124-41-4 ]
[ 304646-29-5 ]

References: [1]Journal of the Chemical Society,1952,p. 4219,4220.

6
[ 1920-66-7 ]
[ 124-40-3 ]
[ 5096-84-4 ]

References: [1]Journal of the Chemical Society,1951,p. 474,478.
Journal of the Chemical Society,1952,p. 4219,4224.

7
[ 1920-66-7 ]
[ 109-89-7 ]
[ 856973-04-1 ]

References: [1]Journal of the Chemical Society,1951,p. 59l, 592.

8
[ 1920-66-7 ]
[ 74-89-5 ]
[ 5096-83-3 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 60℃; for 2h;	A mixture of <strong>[1920-66-7]2-chloro-5-nitropyrimidin-4-amine</strong> (1.0 g, 5.8 mmol) and methylamine (2.0 M solution in THF, 14 mL, 28 mmol) was allowed to stir in a sealed vessel for 1 h. The mixture was then heated to 60 deg. C. for 30 min. The reaction was cooled to ambient temperature, and an additional amount of methylamine (2.0 M solution in THF, 8 mL, 16 mmol) was added and the reaction was sealed and heated to 60 deg. C. for 30 min. The reaction was cooled, diluted with water, and the precipitate was collected by filtration. The solid was rinsed with small portions of water followed by diethyl ether. The material was dried in under reduced pressure to give N2-methyl-5-nitropyrimidine-2,4-diamine 48 as a light yellow solid. MS (ES+): 170 (M+H)+; Calc. for C5H7N5O2=169.14.

References: [1]Journal of the Chemical Society,1952,p. 4219,4220.
[2]Patent: US2007/72862,2007,A1 .Location in patent: Page/Page column 84.

9
[ 1920-66-7 ]
[ 104-78-9 ]
[ 102880-68-2 ]

References: [1]Journal of the Chemical Society,1956,p. 2000,2003.

10
[ 1920-66-7 ]
[ 13754-19-3 ]

References: [1]Chemische Berichte,1906,vol. 39,p. 252.

11
[ 1920-66-7 ]
[ 14631-08-4 ]

Yield	Reaction Conditions	Operation in experiment
54.5%	With water; iron; ammonium chloride; In ethanol; at 100℃; for 4h;	To a solution of compound 21-2 (20 g, 114.6 mmol) in EtOH/H2O (4/1, 400 mL) was added iron powder (64 g, 1146 mmol) and NH4Cl (aq., 62 g, 1146 mmol), the reaction solution was stirred at 100 C. for 4 h, followed by filtration. The filter cake was washed with MeOH (10 mL×3) and the filtrate was concentrated to give compound 21-3 (9 g, Yield 54.5%) as yellow solid.
49%	With tin(II) chloride dihdyrate; In ethanol; at 80℃; for 2h;Inert atmosphere;	Step-1: 2-chloropyrimidine-4,5-diamine [0176] A mixture of <strong>[1920-66-7]2-chloro-5-nitropyrimidin-4-amine</strong> (1.0 g, 5.7 mmol) and SnCl2·2H2O (5.2 g, 22.9 mmol) in EtOH (55 mL) under N2 was heated to 80 C and stirred for two hours. The mixture was then concentrated under reduced pressure. EtOAc and Celite were added to the residue and the mixture was basified with saturated Na2CO3 (aq.) to pH 9- 10. The mixture was filtered through a pad of Celite and washed with EtOAc. The organic layer was separated and washed with brine, dried (Na2SO4) and concentrated in vacuum. The residue was purified on ISCO (20 g silica gel column, EtOAc/hexanes 0~100%) to give the title compound (0.41 g, 49%).
33%	With iron; ammonium chloride; In tetrahydrofuran; ethanol; water;Reflux;	General procedure: Commercial 1a (50mmol) was dissolved in dichloromethane (80mL), mixture was cooled to 0C, solution of NH3 in MeOH (4mol/L, 12.5mL) was added by dripping slowly, after 30min, the mixture maintained at 0C for 1h. The reaction mixture was filtered, and the insoluble material was washed with ethyl acetate (20mL) and water (30mL) to get 2a (8.66g), yield 90%. Compound 2a (50mmol) was dissolved in THF (40mL), then absolute ethyl alcohol (20mL), water (20mL), Fe (4eq) and ammonium chloride (2eq) were added. The mixture was refluxed until raw material disappeared. The reaction mixture was filtered and filter liquor was evaporated by reducing pressure to get 3a (2.4g), yield 33%. Compound 3a (17mmol) was dissolved in DMF (30mL), triethylamine (3eq) was added, and acetyl isothiocyanate (1eq) was added by dripping slowly, the mixture was stirred at room temperature for 30min, then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.5eq) was added and stirred overnight at room temperature. Pulled the mixture into ice water, using concentrated HCl regulates pH to 1, the mixture was filtered, the residue was dried and washed by water to give 4a (2.0g), yield 60%. Compound 4a (10mmol), 5a/5b/5c/5d/5e (1.2eq), 120mL 1,4-dioxane, 10mL water, Pd(dppf)Cl2 (0.1eq), and NaHCO3 (1eq) were added to a round-bottomed flask, mixture was stirred for 12h at 90C. Solvent was removed by reduced pressure distillation, residue was purified by preparative HPLC (MeCN+0.05% TFA, H2O 0.1%+TFA), Ta-e were finally obtained from above steps, yield 0.58-5.5%.

With water; ammonium chloride;iron; In tetrahydrofuran; ethanol; for 3h;Reflux;

(2) The mixture of the above-mentioned product (41 g), reduced iron (52 g), ammonium chloride (25 g), tetrahydrofuran (200 ml), ethanol (100 ml) and water (100 ml) was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature and was filtered through Celite, and ethanol was then evaporated under reduced pressure. The crystals precipitated were collected by filtration and was dried to give 2-chloropyrimidin-4,5-diamine 28 g. 1H-NMR (DMSO-d6) delta: 4.89 (2H, br s), 6.89 (2H, br s), 7.40 (1H, s).

References: [1]Patent: US2017/313683,2017,A1 .Location in patent: Paragraph 0544.
[2]Patent: WO2016/171755,2016,A1 .Location in patent: Paragraph 0176.
[3]Bioorganic Chemistry,2020,vol. 98.
[4]Journal of Organic Chemistry,1955,vol. 20,p. 829,833,835.
[5]Nature,1948,vol. 162,p. 524.
[6]Patent: US2012/172347,2012,A1 .Location in patent: Page/Page column 35.

12
[ 1920-66-7 ]
[ 14623-58-6 ]

References: [1]Journal of the American Chemical Society,1947,vol. 69,p. 2553.
[2]Journal of Applied Chemistry,1952,vol. 2,p. 239.

13
[ 1920-66-7 ]
[ 18620-73-0 ]

References: [1]Journal of the Chemical Society,1951,p. 474,478.
Journal of the Chemical Society,1952,p. 4219,4224.

14
[ 49845-33-2 ]
[ 1920-66-7 ]

Yield	Reaction Conditions	Operation in experiment
92.6%	With ammonium hydroxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 1h;	To a solution of NH3.H2O (aq., 24 mL) and DIPEA (37.2 mL) in DCM (400 mL) was added dropwise a solution of compound 21-1 (30 g, 15436 mmol) in DCM at 0 C., and the reaction solution was stirred at 0 C. for 1 h, followed by filtration. The filter cake was dried to give compound 21-2 (25 g, Yield 92.6%) as yellow solid. LCMS (ESI) m/z: 175.0 (M+1)
90.1%	With ammonia; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; at 0℃; for 1h;	Aqueous ammonia(8.0ml) and N,N-diisopropylethylamine(13.2ml) were dissolved into 150ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitropyrimidine(10.0g) in dichloromethane(30ml) at 0C. After the completion of the dropwise addition, the mixture was kept at the same temperature to react for 1 hour. The precipitate was filtered off. The filter cake was recrystallized to obtain a yellow solid(8.1g) in a yield of 90.1%. 1H NMR(400 MHz, DMSO-d6): delta 9.20(s, 1H), 9.02(s, 1H), 8.60(s, 1H)ppm.
90%	With ammonia; In methanol; dichloromethane; at 0℃; for 1.5h;	General procedure: Commercial 1a (50mmol) was dissolved in dichloromethane (80mL), mixture was cooled to 0C, solution of NH3 in MeOH (4mol/L, 12.5mL) was added by dripping slowly, after 30min, the mixture maintained at 0C for 1h. The reaction mixture was filtered, and the insoluble material was washed with ethyl acetate (20mL) and water (30mL) to get 2a (8.66g), yield 90%. Compound 2a (50mmol) was dissolved in THF (40mL), then absolute ethyl alcohol (20mL), water (20mL), Fe (4eq) and ammonium chloride (2eq) were added. The mixture was refluxed until raw material disappeared. The reaction mixture was filtered and filter liquor was evaporated by reducing pressure to get 3a (2.4g), yield 33%. Compound 3a (17mmol) was dissolved in DMF (30mL), triethylamine (3eq) was added, and acetyl isothiocyanate (1eq) was added by dripping slowly, the mixture was stirred at room temperature for 30min, then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.5eq) was added and stirred overnight at room temperature. Pulled the mixture into ice water, using concentrated HCl regulates pH to 1, the mixture was filtered, the residue was dried and washed by water to give 4a (2.0g), yield 60%. Compound 4a (10mmol), 5a/5b/5c/5d/5e (1.2eq), 120mL 1,4-dioxane, 10mL water, Pd(dppf)Cl2 (0.1eq), and NaHCO3 (1eq) were added to a round-bottomed flask, mixture was stirred for 12h at 90C. Solvent was removed by reduced pressure distillation, residue was purified by preparative HPLC (MeCN+0.05% TFA, H2O 0.1%+TFA), Ta-e were finally obtained from above steps, yield 0.58-5.5%.

89%	With ammonia; In ethanol; dichloromethane; at 0℃;	A solution of 2,4-dichloro-5-nitropyrimidine (14) (0.90 g, 4.64 mmol)in DCM (6.7 mL, 0.7 M) was added dropwise to a solution of 2 MAmmonia in EtOH (6 mL) stirring at 0 C. The reaction was stirred for30 min at 0 C, after which the mixture was warmed to RT and the solventremoved in vacuo.40 The crude residue was purified via silica gel chromatography(4:1 Hexanes:EtOAc) to afford the desired compound as ayellow solid (2.40 g, 13.8 mmol, 89%). Rf 0.24 (4:1 Hexanes:EtOAc); M.p.212-213 C (Lit.=220-221)41; IR (cm-1) 3430, 3056, 1642, 1579, 1534;1H NMR (400 MHz, DMSO-d6) 8.58 (1H, s, NH2), 9.02 (1H, s, H-6), 9.19(1H, s, NH2); 13C NMR (100 MHz, DMSO-d6) delta 127.0 (Ar-C), 157.5 (Ar-C),158.0 (Ar-C), 162.6 (Ar-C); HRMS cal. C4H2ClN4O2 (ES-) m/z 172.986629[M-H]-, found 172.988897.
84%	With ammonium hydroxide; sodium hydroxide; In tetrahydrofuran; at 55℃; for 2h;	To 2,4-dichloro-5-nitropyrimidine (500 mg, 2.5 mmol) dissolved in tetrahydrofuran (10 mL), sodium hydroxide (238 mg, 2.8 mmol) and aqueous ammonia (0.3 mL) was added, and reacted for 2 hrs at 55C. The solvent was removed under reduced pressure, and the residue was separated by flash column chromatography (dichloromethane: methanol=100:1), to obtain Compound w: 2-chloro-5-nitro-4-aminopyrimidine as a white solid (0.47 g, yield 84%). MS(ESI)m/z: [M+H]+=175.
	With ammonia; In water; ethyl acetate; at 20℃; for 1h;	To a solution of 5 g (25 mmol) 2,4-dichloro-5-nitro-pyrimdine in 150 mL EtOAc was added 50 mL 28-34% aqueous NH4OH. After stirred at rt for 1 hour, the reaction mixture was filtered. The organic layer was concentrated to give desired solid product. 1H NMR (CD3OD): 9.03 (1H, s). LC-MS [M+H]=175.
	With ammonia; In water; at 0℃; for 0.5h;	To a rapidly stirred solution of saturated aqueous ammonium hydroxide (50 mL) and ice in a 0 deg. C. bath was added 2,4-dichloro-5-nitropyrimidine (6.0 g, 31 mmol) in portions. The resulting yellow foamy mixture was allowed to stir for 30 min, at which point the precipitate was isolated by filtration. The solid was rinsed several times with ice-cold water and once with ice cold ethanol to give a peach-colored solid. The crude solid was purified by adsorption onto 18 g silica gel, followed by silica gel chromatography, eluding with 0-20% MeOH/dichloromethane to give 2-chloro-5-nitropyrimidin-4-amine as an off-white solid. MS (ES+): 175 (M+H)+; Calc. for C4H3ClN4O2=174.55.
	With ammonia; In ethanol; dichloromethane; at 0℃; for 0.333333h;	(1) To a solution of 2,4-dichloro-5-nitropyrimidine (50 g) in dichloromethane (400 ml) was added dropwise 2 mol/L ammonia/ethanol solution (387 mL) at 0 C. and the mixture was stirred at the same temperature for 20 minutes. The crystals precipitated were collected by filtration and was washed with ethyl acetate (100 ml) and water (150 ml), and was then dried to give 2-chloro-5-nitropyrimidin-4-amine 42 g. 1H-NMR (DMSO-d6) delta: 8.59 (1H, br s), 9.02 (1H, s), 9.19 (1H, br s).

References: [1]Patent: US2017/313683,2017,A1 .Location in patent: Paragraph 0541-0542.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 10685 - 10699.
[3]Patent: EP2578584,2013,A1 .Location in patent: Paragraph 0071; 0072.
[4]Bioorganic Chemistry,2020,vol. 98.
[5]Bioorganic and Medicinal Chemistry,2020,vol. 28.
[6]ChemMedChem,2019,vol. 14,p. 952 - 964.
[7]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 321 - 328.
[8]Patent: EP3284743,2018,A1 .Location in patent: Paragraph 0135.
[9]Chemische Berichte,1906,vol. 39,p. 252.
[10]Journal of Applied Chemistry,1952,vol. 2,p. 239.
[11]Journal of Medicinal Chemistry,1992,vol. 35,p. 4455 - 4463.
[12]Patent: US2005/250779,2005,A1 .Location in patent: Page/Page column 5.
[13]Patent: US2007/72862,2007,A1 .Location in patent: Page/Page column 83-84.
[14]Patent: US2012/172347,2012,A1 .Location in patent: Page/Page column 35.

15
[ 110-91-8 ]
[ 1920-66-7 ]
[ 1141-28-2 ]

References: [1]Chemistry of Heterocyclic Compounds,1989,vol. 25,p. 936 - 943.
Khimiya Geterotsiklicheskikh Soedinenii,1989,p. 1118 - 1125.
[2]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 321 - 328.

16
[ 109-01-3 ]
[ 1920-66-7 ]
[ 124732-29-2 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1053 - 1059.
[2]Heterocycles,1991,vol. 32,p. 2093 - 2097.

17
[ 288-32-4 ]
[ 1920-66-7 ]
[ 131885-71-7 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4455 - 4463.

18
[ 1920-66-7 ]
[ 113-00-8 ]
[ 84097-27-8 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 917 - 921.

19
[ 1920-66-7 ]
[ 108-98-5 ]
[ 124732-28-1 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1053 - 1059.

21
[ 1920-66-7 ]
[ 10034-85-2 ]
phosphonium iodide [ No CAS ]
[ 13754-19-3 ]

References: [1]Chemische Berichte,1906,vol. 39,p. 252.

23
[ 7664-41-7 ]
[ 49845-33-2 ]
[ 1920-66-7 ]

References: [1]Chemische Berichte,1906,vol. 39,p. 252.

24
[ 6165-69-1 ]
[ 1920-66-7 ]
4-amino-5-nitro-2-(3-thiophene)pyrimidine [ No CAS ]