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5466-43-3

5466-43-3

Identification

  • Product Name:5H-Cyclopentapyrimidine,2,4-dichloro-6,7-dihydro-

  • CAS Number: 5466-43-3

  • EINECS:

  • Molecular Weight:189.044

  • Molecular Formula: C7H6Cl2N2

  • HS Code:2933990090

  • Mol File:5466-43-3.mol

Synonyms:2,4-Dichloro-5,6-trimethylenepyrimidine;2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine;NSC 27369;2,4-Dichloro-5H,6H,7H-cyclopenta[d]pyrimidine;

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Safety information and MSDS

  • Pictogram(s):Xn

  • Hazard Codes:Xn

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  • Manufacture/Brand:TRC
  • Product Description:2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine
  • Packaging:10mg
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2,4-Dichloro-5H,6H,7H-cyclopenta[d]pyrimidine 95%
  • Packaging:5 g
  • Price:$ 584
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2,4-Dichloro-5H,6H,7H-cyclopenta[d]pyrimidine 95%
  • Packaging:1 g
  • Price:$ 176
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine 95%
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  • Price:$ 94.2
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2,4-Dichloro-5H,6H,7H-cyclopenta[d]pyrimidine >95%
  • Packaging:500mg
  • Price:$ 342
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  • Manufacture/Brand:Labseeker
  • Product Description:2,4-dichloro-6,7-dihydro-5H-cyclopenta[d][1,3]chlorazine 98
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  • Price:$ 800
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  • Manufacture/Brand:Labseeker
  • Product Description:2,4-dichloro-6,7-dihydro-5H-cyclopenta[d][1,3]chlorazine 98
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  • Manufacture/Brand:ChemScene
  • Product Description:2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine 99.87%
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  • Manufacture/Brand:ChemScene
  • Product Description:2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine 99.87%
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  • Manufacture/Brand:ChemScene
  • Product Description:2,4-Dichloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine 99.87%
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Relevant articles and documentsAll total 26 Articles be found

METHODS OF USE FOR PYRIMIDINES AS FERROPORTIN INHIBITORS

-

Paragraph 798-802, (2021/11/06)

The subject matter described herein is directed to ferroportin inhibitor compounds of Formula (I) and pharmaceutical salts thereof, methods of preparing the compounds, pharmaceutical compositions comprising the compounds, and methods of administering the compounds for prophylaxis and/or treatment of diseases caused by a lack of hepcidin or iron metabolism disorders, particularly iron overload states, such as thalassemia, sickle cell disease and hemochromatosis, and also kidney injuries.

Methylpyrazole derivatives as RET inhibitor

-

, (2021/07/21)

The invention relates to a methylpyrazole derivative as an RET inhibitor, in particular to a compound as shown in a formula (I), a stereoisomer and pharmaceutically acceptable salt thereof, a preparation method and a pharmaceutical composition thereof. The compound of the formula (I) can be used for preventing or treating diseases mediated by abnormal RET activity.

Matrix Metalloproteinase 13 Inhibitors for Modulation of Osteoclastogenesis: Enhancement of Solubility and Stability

Knapinska, Anna M.,Singh, Chandani,Drotleff, Gary,Blanco, Daniela,Chai, Cedric,Schwab, Jason,Herd, Anu,Fields, Gregg B.

supporting information, p. 1133 - 1142 (2021/01/29)

Matrix metalloproteinase 13 (MMP-13) activity has been correlated to breast cancer bone metastasis. It has been proposed that MMP-13 contributes to bone metastasis through the promotion of osteoclastogenesis. To explore the mechanisms of MMP-13 action, we previously described a highly efficacious and selective MMP-13 inhibitor, RF036. Unfortunately, further pursuit of RF036 as a probe of MMP-13 in vitro and in vivo activities was not practical due to the limited solubility and stability of the inhibitor. Our new study has explored replacing the RF036 backbone sulfur atom and terminal methyl group to create inhibitors with more favorable pharmacokinetic properties. One compound, designated inhibitor 3, in which the backbone sulfur and terminal methyl group of RF036 were replaced by nitrogen and oxetane, respectively, had comparable activity, selectivity, and membrane permeability to RF036, while exhibiting greatly enhanced solubility and stability. Inhibitor 3 effectively inhibited MMP-13-mediated osteoclastogenesis but spared collagenolysis, and thus represents a next-generation MMP-13 probe applicable for in vivo studies of breast cancer metastasis.

Discovery of novel pyrimidine molecules containing boronic acid as VCP/p97 Inhibitors

Zhang, Yonglei,Xie, Xiaomin,Wang, Xueyuan,Wen, Tiantian,Zhao, Chi,Liu, Hailong,Zhao, Bo,Zhu, Yongqiang

, (2021/04/12)

Valine-containing protein (VCP) is a member of the adenosine triphosphate family involved in a variety of cellular activities. VCP/p97 is capable of maintaining protein homeostasis and mediating the degradation of misfolded polypeptides by the ubiquitin–proteasome system (UPS). In this manuscript, a series of novel p97 inhibitors with pyrimidine as core structure were designed, synthesized and biologically evaluated. Based on the enzymatic results, a detailed structure–activity relationship discussion of the synthesized compounds was carried out. Furthermore, cellular activities of the compounds with enzymatic potency of less than 200 nM were investigated by using A549 and RPMI8226 cell lines. Among the screened inhibitors, compound 17 (IC50, 54.7 nM) showed good enzymatic activity. Investigation of cellular activities with non-small cell lung cancer A549 and multiple myeloma (MM) RPMI8226 further confirmed the potency of 17 with the IC50 values of 2.80 μM and 0.86 μM, respectively. Compound 17 is now being developed as a candidate. Finally, docking studies were carried out to explore the possible binding mode between the active inhibitor 17 and p97.

Synthesis and evaluation of novel fused pyrimidine derivatives as GPR119 agonists

Fang, Yuanying,Xiong, Lijuan,Hu, Jianguo,Zhang, Shaokun,Xie, Saisai,Tu, Liangxing,Wan, Yang,Jin, Yi,Li, Xiang,Hu, Shaojie,Yang, Zunhua

, p. 103 - 111 (2019/01/28)

A novel series of fused pyrimidine derivatives were designed, synthesized and evaluated as GPR119 agonists. Among them, cyclohexene fused compounds (tetrahydroquinazolines) showed greater GPR119 agonistic activities than did dihydrocyclopentapyrimidine and tetrahydropyridopyrimidine scaffolds. Analogues (16, 19, 26, 28, 42) bearing endo-N-Boc-nortropane amine and fluoro-substituted aniline exhibited better EC50 values (0.27–1.2 μM) though they appeared to be partial agonists.

Process route upstream and downstream products

Process route

6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol
5466-00-2

6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
With trichlorophosphate; for 1h; Heating;
94%
With trichlorophosphate; at 110 ℃; for 12h;
92%
With trichlorophosphate; at 20 - 60 ℃; for 3h;
90%
With trichlorophosphate; for 5h; Heating / reflux;
83%
With trichlorophosphate; at 100 ℃; for 3h;
81%
With trichlorophosphate; for 7h; Reflux;
73%
With trichlorophosphate; Reflux;
67.1%
With N,N-dimethyl-aniline; trichlorophosphate; for 2h; Reflux;
61%
With P,P-dichlorophenylphosphine oxide; at 135 ℃;
53%
With trichlorophosphate; In N,N-dimethyl-aniline; for 3h; Reflux;
43%
With trichlorophosphate;
With trichlorophosphate; for 2h; Heating;
19 g
With trichlorophosphate;
With trichlorophosphate; at 20 ℃; for 2h;
With trichlorophosphate; at 130 ℃;
13 g
With trichlorophosphate; at 110 ℃; for 5h; Inert atmosphere;
2.5 g
1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione
5466-00-2

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
With trichlorophosphate; at 120 ℃; for 2h;
86.1%
With trichlorophosphate; at 120 ℃; for 2h;
80%
With sodium hydrogencarbonate; trichlorophosphate; at 85 - 100 ℃; for 24h; Cooling with ice;
70%
With N,N-dimethyl-formamide; trichlorophosphate; Reflux;
With trichlorophosphate; at 105 ℃; for 0.5h;
methyl 2-oxocyclopentane-1-carboxylate
10472-24-9,265317-94-0

methyl 2-oxocyclopentane-1-carboxylate

urea
57-13-6

urea

6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol
5466-00-2

6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
methyl 2-oxocyclopentane-1-carboxylate; urea; With hydrogenchloride; In ethanol; water; for 3h; Reflux;
6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol; With sodium hydroxide; In water; for 2h; Reflux;
With trichlorophosphate; In water; at 0 ℃; for 4h; pH=3; Reflux;
24%
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

urea
57-13-6

urea

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
2-ethoxycarbonyl-1-cyclopentanone; urea; With hydrogenchloride; In ethanol; water; at 80 ℃; for 4h;
With sodium hydroxide; In water; at 110 ℃; for 1h;
With hydrogenchloride; trichlorophosphate; more than 3 stages;
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 40 g / ethanol / 5 h / 160 °C
2: 19 g / POCl3 / 2 h / Heating
With trichlorophosphate; In ethanol;
Multi-step reaction with 3 steps
1: conc. hydrochloric acid / ethanol / 4 h / Heating
2: 5 percent aqu. sodium hydroxide / 1 h / Heating
3: 94 percent / phosphorous oxychloride / 1 h / Heating
With hydrogenchloride; sodium hydroxide; trichlorophosphate; In ethanol;
Multi-step reaction with 2 steps
1: hydrogenchloride / ethanol; water / 2 h / Reflux
2: trichlorophosphate; N,N-dimethyl-aniline / 2 h / Reflux
With hydrogenchloride; N,N-dimethyl-aniline; trichlorophosphate; In ethanol; water;
Multi-step reaction with 2 steps
1.1: hydrogenchloride / ethanol / 5.5 h / 85 °C / Cooling with ice
1.2: 2 h / Reflux
2.1: trichlorophosphate / 3 h / 100 °C
With hydrogenchloride; trichlorophosphate; In ethanol;
Multi-step reaction with 2 steps
1: hydrogenchloride / water; ethanol / 2.5 h / Reflux
2: trichlorophosphate / Reflux
With hydrogenchloride; trichlorophosphate; In ethanol; water;
Multi-step reaction with 2 steps
1: hydrogenchloride / ethanol; water
2: trichlorophosphate / 12 h / 110 °C
With hydrogenchloride; trichlorophosphate; In ethanol; water;
Multi-step reaction with 3 steps
1: sodium carbonate / water / 48 h / 20 °C
2: acetic acid / water / 72 h / Reflux
3: trichlorophosphate / 130 °C
With sodium carbonate; acetic acid; trichlorophosphate; In water;
Multi-step reaction with 2 steps
1: hydrogenchloride / ethanol; water / 24 h / 80 °C
2: trichlorophosphate / 0.5 h / 105 °C
With hydrogenchloride; trichlorophosphate; In ethanol; water;
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water; ethanol / 4 h / 80 °C
1.2: 1.5 h / 110 °C
2.1: trichlorophosphate / 2 h / 120 °C
With hydrogenchloride; trichlorophosphate; In ethanol; water;
Multi-step reaction with 2 steps
1: hydrogenchloride / ethanol; water / 4 h / Reflux; Inert atmosphere
2: trichlorophosphate / N,N-dimethyl-aniline / 3 h / Reflux
With hydrogenchloride; trichlorophosphate; In ethanol; water; N,N-dimethyl-aniline;
tert-butyl N-{1-[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]ethyl}-N-methylcarbamate

tert-butyl N-{1-[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]ethyl}-N-methylcarbamate

trifluoroacetic acid
76-05-1

trifluoroacetic acid

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
In dichloromethane; at 25 ℃; for 3h;
methyl 2-oxocyclopentane-1-carboxylate
10472-24-9,265317-94-0

methyl 2-oxocyclopentane-1-carboxylate

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: chloro-trimethyl-silane / N,N-dimethyl-formamide / 0 - 20 °C
2: trichlorophosphate; sodium hydrogencarbonate / 24 h / 85 - 100 °C / Cooling with ice
With chloro-trimethyl-silane; sodium hydrogencarbonate; trichlorophosphate; In N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: 0.2 h / Microwave irradiation
2: trichlorophosphate / 2 h / 20 °C
With trichlorophosphate;
Multi-step reaction with 2 steps
1: 0.17 h / Microwave irradiation
2: P,P-dichlorophenylphosphine oxide / 135 °C
With P,P-dichlorophenylphosphine oxide;
Multi-step reaction with 2 steps
1: sodium methylate / ethanol / 0 - 60 °C / Inert atmosphere
2: trichlorophosphate / 7 h / Reflux
With sodium methylate; trichlorophosphate; In ethanol;
Multi-step reaction with 3 steps
1: hydrogenchloride / ethanol; water / 4 h / 80 °C
2: sodium hydroxide / 1.5 h / 110 °C
3: trichlorophosphate / 2 h / 120 °C
With hydrogenchloride; sodium hydroxide; trichlorophosphate; In ethanol; water;
Multi-step reaction with 2 steps
1.1: chloro-trimethyl-silane / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
1.2: 1 h / 0 - 70 °C
2.1: trichlorophosphate / 5 h / 110 °C / Inert atmosphere
With chloro-trimethyl-silane; trichlorophosphate; In N,N-dimethyl-formamide;
2-(methylthio)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol
3087-14-7

2-(methylthio)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: acetic acid / water / 72 h / Reflux
2: trichlorophosphate / 130 °C
With acetic acid; trichlorophosphate; In water;
2-ureido-1-carbethoxycyclopent-1-ene
18227-09-3

2-ureido-1-carbethoxycyclopent-1-ene

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 5 percent aqu. sodium hydroxide / 1 h / Heating
2: 94 percent / phosphorous oxychloride / 1 h / Heating
With sodium hydroxide; trichlorophosphate;
methyl 2-ureidocyclopentene-1-carboxylate
1196101-51-5

methyl 2-ureidocyclopentene-1-carboxylate

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine
5466-43-3

2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium hydroxide / 1.5 h / 110 °C
2: trichlorophosphate / 2 h / 120 °C
With sodium hydroxide; trichlorophosphate;

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