1-[(1S,2R,3S)-2-fluoro-3-(hydroxymethyl)cyclopentyl]pyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-[(1S,2R,3S)-2-fluoro-3-(hydroxymethyl)cyclopentyl]pyrimidine-2,4(1H,3H)-dione
• CAS No.: 129746-09-4
• Molecular Formula: C₁₀H₁₃FN₂O₃
• Molecular Weight: 228.223
• Mol file: 129746-09-4.mol

Synonyms:2,4(1H,3H)-Pyrimidinedione,1-[2-fluoro-3-(hydroxymethyl)cyclopentyl]-, (1a,2a,3a)- (9CI);2,4(1H,3H)-Pyrimidinedione, 1-[2-fluoro-3-(hydroxymethyl)cyclopentyl]-, (1a,2a,3a)-(?à)-

Chemical Property of 1-[(1S,2R,3S)-2-fluoro-3-(hydroxymethyl)cyclopentyl]pyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 75.35000
• Density: 1.4g/cm³
• LogP: 0.23040

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[(1S,2R,3S)-2-fluoro-3-(hydroxymethyl)cyclopentyl]pyrimidine-2,4(1H,3H)-dione

There total 15 articles about 1-[(1S,2R,3S)-2-fluoro-3-(hydroxymethyl)cyclopentyl]pyrimidine-2,4(1H,3H)-dione 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:

triphenylmethoxymethylcyclopent-2-ene (119895-90-8) → 1-((1R,2R,3R)-2-Fluoro-3-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione (129746-09-4,129829-87-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) dimethyldibromohydantoin, 2.) K₂CO₃ / 1.) H₂O, acetone, 0 deg C, 2.) MeOH

2: 84 percent / NaN₃, NH₄Cl / ethanol; H₂O / 90 °C

3: diethylaminosulphur trifluoride (DAST) / CH₂Cl₂ / 0 °C

4: H₂ / Lindlar catalyst / ethanol

5: benzene; dimethylformamide / 18 h / -15 - 20 °C

6: toluene-p-sulphonic acid / methanol; CH₂Cl₂

7: HCl / 0.5 h / Heating

With hydrogenchloride; sodium azide; dimethyldibromohydantoin; diethylamino-sulfur trifluoride; hydrogen; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; Lindlar's catalyst; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39900000151

Reference yield:

triphenylmethoxymethylcyclopent-2-ene (119895-90-8) → 1-((1R,2S,3R)-2-Fluoro-3-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione (129746-09-4,129829-87-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) dimethyldibromohydantoin, 2.) K₂CO₃ / 1.) H₂O, acetone, 0 deg C, 2.) MeOH

2: 84 percent / NaN₃, NH₄Cl / ethanol; H₂O / 90 °C

3: pyridine

4: Bu₄NF / tetrahydrofuran

5: 100 percent / H₂ / Lindlar catalyst / ethanol

6: benzene; dimethylformamide / 18 h / -15 - 20 °C

7: toluene-p-sulphonic acid / methanol; CH₂Cl₂

8: HCl / 0.5 h / Heating

With pyridine; hydrogenchloride; sodium azide; dimethyldibromohydantoin; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39900000151

Reference yield:

2-exo-triphenylmethoxymethyl-6-oxabicyclo<3.1.0>hexane (119895-91-9,129829-81-8,129829-82-9,137767-65-8,137767-66-9) → 1-((1R,2R,3R)-2-Fluoro-3-hydroxymethyl-cyclopentyl)-1H-pyrimidine-2,4-dione (129746-09-4,129829-87-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / NaN₃, NH₄Cl / ethanol; H₂O / 90 °C

2: diethylaminosulphur trifluoride (DAST) / CH₂Cl₂ / 0 °C

3: H₂ / Lindlar catalyst / ethanol

4: benzene; dimethylformamide / 18 h / -15 - 20 °C

5: toluene-p-sulphonic acid / methanol; CH₂Cl₂

6: HCl / 0.5 h / Heating

With hydrogenchloride; sodium azide; diethylamino-sulfur trifluoride; hydrogen; ammonium chloride; toluene-4-sulfonic acid; Lindlar's catalyst; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1039/c39900000151

upstream raw materials:

triphenylmethoxymethylcyclopent-2-ene

2-exo-triphenylmethoxymethyl-6-oxabicyclo<3.1.0>hexane

(1β,2α,3β)-2-fluoro-3-triphenylmethoxymethylcyclopentylamine

(1S,2R,3S)-2-Fluoro-3-trityloxymethyl-cyclopentylamine