2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (R)-

Base Information

• Chemical Name: 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (R)-
• CAS No.: 37076-68-9
• Molecular Formula: C8H9FN2O3
• Molecular Weight: 200.169
• Hs Code.: 2942000000
• NSC Number: 200695,148958
• UNII: 5317337V7V
• DSSTox Substance ID: DTXSID8021305
• Nikkaji Number: J96.662B
• Wikidata: Q27261036
• ChEMBL ID: CHEMBL235993
• Mol file: 37076-68-9.mol

Synonyms:37076-68-9;(R)-Tegafur;(R)-Ftorafur;Tegafur, (R)-;Ftorafur, (R)-;2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (R)-;5-fluoro-1-[(2R)-oxolan-2-yl]pyrimidine-2,4-dione;CHEMBL235993;DTXSID8021305;UNII-5317337V7V;NSC148958;NSC-200695;R-1-(Tetrahydrofuran-2-yl)-5-fluorouracil;5317337V7V;Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-, (R)-;DTXCID801436391;5-fluoro-1-[(2R)-oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione;CAS-37076-68-9;C8-H9-F-N2-O3;2,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (R)-;2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-((2R)-tetrahydro-2-furanyl)-;NCGC00159418-02;NCGC00159418-05;2-Cyclohexene-1-one??;NCIMech_000223;SCHEMBL4553;Tox21_111649;Tox21_301812;BDBM50247894;CCG-35341;CCG-36092;NSC200695;s1300;AKOS024306980;Tox21_111649_1;NCGC00255222-01;NCGC00386138-01;BT166256;NCI60_001026;Tegafur (FT-207, NSC 148958);F0635;SW220241-1;5-Fluoro-1-[(R)-tetrahydrofuran-2-yl]uracil;AB01566812_01;EN300-8676918;A823522;5-fluoro-1-[(2R)-2-oxolanyl]pyrimidine-2,4-dione;Q27261036;5-fluoranyl-1-[(2R)-oxolan-2-yl]pyrimidine-2,4-dione;5-fluoro-1-(R)-tetrahydro-furan-2-yl-1H-pyrimidine-2,4-dione, AldrichCPR

Chemical Property of 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (R)-

Chemical Property:

• Melting Point: 171-173 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• PSA: 64.09000
• Density: 1.45 g/cm³
• LogP: -0.01530
• Storage Temp.: 2-8°C
• Water Solubility.: 28.02g/L(37 oC)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 200.05972032
• Heavy Atom Count: 14
• Complexity: 316

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tegafur ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1)N2C=C(C(=O)NC2=O)F
• Isomeric SMILES: C1C[C@@H](OC1)N2C=C(C(=O)NC2=O)F

Technology Process of 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (R)-

There total 4 articles about 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-, (R)- 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:

(S)-1-(2,5-dihydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione → (S)-5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (55774-30-6,65732-47-0,79107-97-4) + 5-fluoro-1-((R)-tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione (37076-68-9,65732-47-0,79107-97-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 0.166667h; under 760.051 Torr; Overall yield = 78 %; Overall yield = 16.0 mg;

DOI:10.1021/acs.orglett.7b02332

Reference yield:

1-(4,5-dehydrotetrahydro-2-furanyl)-5-fluorouracil (68723-23-9) → 5-fluoro-1-((R)-tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione (37076-68-9,65732-47-0,79107-97-4)

Guidance literature:

Reference yield:

(S,E)-5-fluoro-1-(1-(hex-2-enyloxy)allyl)pyrimidine-2,4(1H,3H)-dione → (S)-5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (55774-30-6,65732-47-0,79107-97-4) + 5-fluoro-1-((R)-tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione (37076-68-9,65732-47-0,79107-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 0.17 h / 40 °C

2: palladium on activated charcoal; hydrogen / methanol / 0.17 h / 20 °C / 760.05 Torr

With Hoveyda-Grubbs catalyst second generation; palladium on activated charcoal; hydrogen; In methanol; dichloromethane;

DOI:10.1021/acs.orglett.7b02332

upstream raw materials:

1-(4,5-dehydrotetrahydro-2-furanyl)-5-fluorouracil

Downstream raw materials:

5-fluorouracil

Refernces

• 1、 -. "Novel ester precursor intermediates and antipodes for the preparation of 1-(2-tetrahydrofuryl)-5-fluorouracil". . . Retrieved 2008/06/13.