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Cas Database

5466-00-2

5466-00-2

Identification

  • Product Name:5,6-Trimethyleneuracil

  • CAS Number: 5466-00-2

  • EINECS:

  • Molecular Weight:152.153

  • Molecular Formula: C7H8N2O2

  • HS Code:2933990090

  • Mol File:5466-00-2.mol

Synonyms:5,6-trimethyleneuracil;6,7-dihydro-1H,3H,5H-cyclopentapyrimidin-2,4-dione;5,6-cyclopentanouracil;cyclopentanopyrimidine-2,4-dione;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:5,6-Trimethyleneuracil
  • Packaging:250mg
  • Price:$ 70
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:5,6-Trimethyleneuracil
  • Packaging:50mg
  • Price:$ 55
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:6,7-Dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione >95%
  • Packaging:500mg
  • Price:$ 130
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:6,7-Dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione >95%
  • Packaging:1g
  • Price:$ 260
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:6,7-Dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol 97%
  • Packaging:1g
  • Price:$ 414
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:6,7-Dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione >95%
  • Packaging:5g
  • Price:$ 342
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:6,7-Dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione 95+%
  • Packaging:10g
  • Price:$ 341
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:6,7-Dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione 95%
  • Packaging:5g
  • Price:$ 368
  • Delivery:In stock
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  • Manufacture/Brand:Chemcia Scientific
  • Product Description:2-Hydroxy-3,5,6,7-tetrahydro-cyclopentapyrimidin-4-one 97%
  • Packaging:2 G
  • Price:$ 135
  • Delivery:In stock
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  • Manufacture/Brand:Atlantic Research Chemicals
  • Product Description:6,7-Dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione 95%
  • Packaging:1gm:
  • Price:$ 201.47
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Relevant articles and documentsAll total 33 Articles be found

Formation of 5,6-cyclopentano-uracil by cyclization of the bisamide of adipic acid induced by oxalyl chloride

Bergman, Jan,Svensson, Per H.

, p. 4601 - 4603 (2010)

Cyclization of the bisamide of adipic acid induced by oxalyl chloride will eventually yield a product of the composition C9H8N2O5, which upon hydrolysis gave 5,6-cyclo-pentanouracil. The structures of both compounds were established by X-ray crystallography.

Synthesis of new 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione derivatives containing the substituted aliphatic ring

Papoyan,Khachatryan,Panosyan,Kochikyan

, (2012)

The bromination of 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione (1) resulted in the substitution in the aliphatic ring. The reaction of this product with different N-nucleophiles gives new derivatives of the starting compound. The direction of

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.

Methylpyrazole derivatives as RET inhibitor

-

Paragraph 0710-0715, (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.

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.

Synthetic method of medical intermediate cycloalkanopyrimidinedione compound

-

Paragraph 0020-0022; 0050-0055, (2020/12/15)

The invention provides a synthetic method of a cycloalkanopyrimidinedione compound, and belongs to the technical field of organic synthesis. The method provided by the invention comprises the following steps of: taking a 2-methoxycarbonyl naphthenone comp

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

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

Conditions
Conditions Yield
methyl 2-oxocyclopentane-1-carboxylate; urea; With chloro-trimethyl-silane; In N,N-dimethyl-formamide; at 0 - 40 ℃; Inert atmosphere;
With water; sodium hydroxide; at 70 ℃; for 1h;
With hydrogenchloride; In water; pH=~ 2;
79%
With sodium methylate; In ethanol; at 0 - 60 ℃; Inert atmosphere;
48%
for 0.166667h; Microwave irradiation;
40%
for 0.2h; Microwave irradiation;
methyl 2-oxocyclopentane-1-carboxylate; urea; With chloro-trimethyl-silane; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;
With water; sodium hydroxide; at 0 - 70 ℃; for 1h;
4.6 g
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

urea
57-13-6

urea

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione
5466-00-2

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

Conditions
Conditions Yield
With boron trifluoride diethyl etherate; at 135 ℃; for 0.0833333h; Neat (no solvent); Microwave irradiation;
83%
With hydrogenchloride; In ethanol; water; at 80 ℃; for 24h;
73%
With hydrogenchloride; In ethanol; for 3h; Reflux;
60%
With hydrogenchloride; In ethanol; water; for 3h; Reflux;
31%
With ethanol; sodium ethanolate; at 100 ℃;
2-ethoxycarbonyl-1-cyclopentanone; urea; With hydrogenchloride; In ethanol; water; at 80 ℃; for 4h;
With sodium hydroxide; at 110 ℃; for 1.5h;
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

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

Conditions
Conditions Yield
With hydrogenchloride; In ethanol; water;
85%
With hydrogenchloride; In ethanol; water; for 4h; Reflux; Inert atmosphere;
69%
2-ethoxycarbonyl-1-cyclopentanone; urea; hydrogenchloride; In ethanol; water; for 2h; Heating / reflux;
With sodium hydroxide; In water; for 0.5h;
66%
With hydrogenchloride; In ethanol; water; for 2h; Reflux;
66%
2-ethoxycarbonyl-1-cyclopentanone; urea; With hydrogenchloride; In ethanol; at 85 ℃; for 5.5h; Cooling with ice;
With sodium hydroxide; In water; for 2h; Reflux;
52%
With hydrogenchloride; In ethanol; water; for 2.5h; Reflux;
30.8%
In ethanol; at 160 ℃; for 5h;
40 g
methyl 2-ureidocyclopentene-1-carboxylate
1196101-51-5

methyl 2-ureidocyclopentene-1-carboxylate

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

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

Conditions
Conditions Yield
methyl 2-ureidocyclopentene-1-carboxylate; With water; sodium hydroxide; at 20 - 85 ℃;
With hydrogenchloride; In water; at 0 ℃; pH=0 - 1;
99%
methyl 2-oxocyclopentane-1-carboxylate
10472-24-9,265317-94-0

methyl 2-oxocyclopentane-1-carboxylate

urea
57-13-6

urea

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione
5466-00-2

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

Conditions
Conditions Yield
With chloro-trimethyl-silane; In N,N-dimethyl-formamide; at 0 - 20 ℃;
92%
methyl 2-ureidocyclopentene-1-carboxylate
1196101-51-5

methyl 2-ureidocyclopentene-1-carboxylate

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione
5466-00-2

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

Conditions
Conditions Yield
With sodium hydroxide; at 110 ℃; for 1.5h;
97.24%
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

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

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: conc. hydrochloric acid / ethanol / 4 h / Heating
2: 5 percent aqu. sodium hydroxide / 1 h / Heating
With hydrogenchloride; sodium hydroxide; In ethanol;
With urea; In ethanol; acetone;
With urea; In ethanol; acetone;
Multi-step reaction with 2 steps
1: sodium carbonate / water / 48 h / 20 °C
2: acetic acid / water / 72 h / Reflux
With sodium carbonate; acetic acid; In water;
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

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione
5466-00-2

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

Conditions
Conditions Yield
With catalyst 001×7 strong acid ion exchange resin; In ethanol; water; at 80 - 90 ℃; for 10h; Reagent/catalyst;
2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one
35563-27-0

2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione
5466-00-2

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

Conditions
Conditions Yield
With chloroacetic acid; In methanol; for 16h; Heating;
82%
With water; chloroacetic acid;
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

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

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

Conditions
Conditions Yield
With acetic acid; In water; for 72h; Reflux;
13.3 g

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  • Amadis Chemical Co., Ltd.
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  • Finetech Industry Limited
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  • Bide Pharmatech Ltd
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  • Career Henan Chemical Co
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  • Shanghai TBBMed Co.,Ltd
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