5466-00-2

Basic information

• Product Name: 6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol
• Synonyms: 6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol;6,7-Dihydro-1H-cyclopenta[d]pyriMidine-2,4(3H,5H)-dione;1H,2H,3H,4H,5H,6H,7H-cyclopenta[d]pyriMidine-2,4-dione;6,7-Dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H);EOS-60938;1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione
• CAS NO: 5466-00-2
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 5466-00-2.mol
• Article Data: 33

Chemical Properties

• Melting Point: 328～330℃
• Boiling Point: 455.7°C at 760 mmHg
• Flash Point: 229.4°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 6.38E-09mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), DMSO (Slightly, Sonicated)
• CAS DataBase Reference: 6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol(5466-00-2)
• EPA Substance Registry System: 6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol(5466-00-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5466-00-2(Hazardous Substances Data)

Usage

Uses

5,6-Trimethyleneuracil can be used as VCP/p97 inhibitors.

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 4379, 1976 DOI: 10.1016/0040-4039(76)80121-9

InChI:InChI=1/C7H8N2O2/c10-6-4-2-1-3-5(4)8-7(11)9-6/h1-3H2,(H2,8,9,10,11)

Upstream product

• 160234-22-0 2-ethtylthiocyclopentanopyrimidin-4-one 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 1196101-51-5 methyl 2-ureidocyclopentene-1-carboxylate 
• 3087-14-7 2-(methylthio)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol 
• 57-13-6 urea 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 18227-09-3 2-ureido-1-carbethoxycyclopent-1-ene 
• 122364-77-6 2-Ureido-cyclopent-1-enecarboxylic acid butyl ester 
• 33081-06-0 2-amino-6,7-dihydro-3H-cyclopenta[d]pyrimidin-4(5H)-one 
• 35563-27-0 2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one 

Downstream Products

• 49786-32-5 5,6-trimethylene-1,3-dimethyluracil 
• 132332-56-0 1-{2-[4-(4-Fluoro-benzoyl)-piperidin-1-yl]-ethyl}-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione; hydrochloride 
• 160234-23-1 1-(benzyloxymethyl)-cyclopentanopyrimidine-2,4-dione 
• 1621363-03-8 4-(2-(3-fluoro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yloxy)benzoic acid methyl ester 
• 1621363-36-7 2-(4-(2-(thiazol-5-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yloxy)phenyl)acetic acid methylester 
• 1621362-84-2 2-(4-(2-(thiazol-5-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yloxy)phenyl)acetic acid 
• 1621363-37-8 2-(4-(2-bromo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yloxy)phenyl)acetic acid methyl ester 
• 1621362-85-3 2-(4-(2-(2-chlorothiazol-5-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yloxy)phenyl)acetic acid 
• 1621363-38-9 2-(4-(2-(5-cyanothiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yloxy)phenyl)acetic acid methyl ester 
• 1621363-49-2 methyl 2-(4-((2-(1-ethoxyvinyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)oxy)phenyl)acetate 
• 1621363-50-5 methyl 2-(4-((2-(2-bromoacetyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)oxy)phenyl)acetate 
• 1621363-51-6 methyl 2-(4-((2-(2-aminothiazol-4-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)oxy)phenyl)acetate 
• 1621362-95-5 2-(4-((2-(2-chlorothiazol-4-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)oxy)phenyl)acetic acid 
• 1621363-52-7 methyl 2-(4-((2-(5-methylthiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)oxy)phenyl)acetate 

Relevant articles and documents

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

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.

Methylpyrazole derivatives as RET inhibitor

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

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.

Synthesis and evaluation of novel fused pyrimidine derivatives as GPR119 agonists

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.