5-Cyclopropyluracil

Base Information

• Chemical Name: 5-Cyclopropyluracil
• CAS No.: 59698-20-3
• Molecular Formula: C7H8N2O2
• Molecular Weight: 152.153
• Hs Code.: 2933599590
• UNII: S84IH49TJS
• DSSTox Substance ID: DTXSID90426295
• Nikkaji Number: J433.740I
• Wikidata: Q27289035
• Mol file: 59698-20-3.mol

Synonyms:5-Cyclopropyluracil;59698-20-3;5-Cyclopropylpyrimidine-2,4(1H,3H)-dione;5-Cyclopropyl-uracil;5-cyclopropyl-1H-pyrimidine-2,4-dione;5-cyclopropyl-2,4(1h,3h)-pyrimidinedione;UNII-S84IH49TJS;S84IH49TJS;5-cyclopropyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;SCHEMBL3561548;DTXSID90426295;5-cyclopropylpyrimidine-2,4-diol;MFCD06800532;AKOS004118819;SB55913;TS-02014;CS-0257782;EN300-6772353;A1-30086;Q27289035;Z1255489791

Chemical Property of 5-Cyclopropyluracil

Chemical Property:

• Melting Point: 220-222(dec)
• PKA: 9.17±0.10(Predicted)
• PSA: 65.72000
• Density: 1.387±0.06 g/cm3(Predicted)
• LogP: -0.05940
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 152.058577502
• Heavy Atom Count: 11
• Complexity: 253

Purity/Quality:

95% ^*data from raw suppliers

5-Cyclopropylpyrimidine-2,4(1H,3H)-dione 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C2=CNC(=O)NC2=O

Technology Process of 5-Cyclopropyluracil

There total 9 articles about 5-Cyclopropyluracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

5-cyclopropyl-2-thio-2,3-dihydropyrimidine-2,4(1H,3H)-dione (59698-21-4) → 5-cyclopropyl-pyrimidin-2,4-(1H,3H)-dione (59698-20-3)

Guidance literature:

With chloroacetic acid; In water; Heating;

DOI:10.1080/15257779408013234

Reference yield: 79.0%

5-cyclopropyl-2,4-dimethoxypyrimidine → 5-cyclopropyl-pyrimidin-2,4-(1H,3H)-dione (59698-20-3)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 20 ℃;

DOI:10.1039/c6ob02560a

Reference yield:

tri-n-butyl-cyclopropyltin (17857-70-4) + 2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine (33282-64-3) → uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 5-cyclopropyl-pyrimidin-2,4-(1H,3H)-dione (59698-20-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; water; Yield given. Multistep reaction; 1.) 100 deg C, 72 h, 2.) acetone, r.t., 1 h;

DOI:10.1002/jhet.5570280629

upstream raw materials:

5-cyclopropyl-2-thio-2,3-dihydropyrimidine-2,4(1H,3H)-dione

tri-n-butyl-cyclopropyltin

2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine

cyclopropylacetyl chloride

Downstream raw materials:

2,4-dichloro-5-cyclopropylpyrimidine

5-cyclopropyl-1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythropentofuranosyl]uracil

5-cyclopropyl-1-[2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl]uracil

Refernces

• 1、 Guo, Xiurong,Ingale, Sachin A.,Yang, Haozhe,He, Yang,Seela, Frank. "MercuryII-mediated base pairs in DNA: unexpected behavior in metal ion binding and duplex stability induced by 2′-deoxyuridine 5-substituents". . p. 870 - 883. Retrieved 2017/02/05.
• 2、 Xin, Minhang,Wen, Jun,Tang, Feng,Tu, Chongxing,Shen, Han,Zhao, Xinge. "The discovery of novel N-(2-pyrimidinylamino) benzamide derivatives as potent hedgehog signaling pathway inhibitors". supporting information. p. 6777 - 6783. Retrieved 2014/01/06.