1-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 118237-75-5
• Molecular Formula: C₁₁H₁₄N₂O₃
• Molecular Weight: 222.244
• Mol file: 118237-75-5.mol

Synonyms:2,4(1H,3H)-Pyrimidinedione,1-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-5-methyl-, cis- (9CI);2,4(1H,3H)-Pyrimidinedione, 1-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-5-methyl-,cis-(?à)-; NSC 615824

Chemical Property of 1-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

• PSA: 75.35000
• Density: 1.291g/cm³
• LogP: 0.36680

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

There total 17 articles about 1-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl]-5-methylpyrimidine-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: 97.0%

Acetic acid (1R,4S)-4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopent-2-enylmethyl ester → (+/-)-1-(4'β-Hydroxymethylcyclopent-2'-en-1'β-yl)-5-methyl-2,4(1H,3H)-pyrimidinedione (118237-75-5,132151-62-3)

Guidance literature:

With methanol; sodium; Ambient temperature;

DOI:10.1016/S0040-4020(97)10380-5

Reference yield: 93.0%

(+/-)-4β-Hydroxymethyl-1β-cyclopent-2-ene (131220-00-3,132203-16-8) → (+/-)-1-(4'β-Hydroxymethylcyclopent-2'-en-1'β-yl)-5-methyl-2,4(1H,3H)-pyrimidinedione (118237-75-5,132151-62-3)

Guidance literature:

With ammonium hydroxide; In methanol; at 85 ℃; for 24h;

DOI:10.1248/cpb.39.1682

Reference yield:

methyl cis-(4-hydroxy-2-cyclopenten-1-yl)acetate (74877-20-6,83338-93-6,120052-54-2) → (+/-)-1-(4'β-Hydroxymethylcyclopent-2'-en-1'β-yl)-5-methyl-2,4(1H,3H)-pyrimidinedione (118237-75-5,132151-62-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) KOH / 1) 1,4-dioxane, reflux, 1 h; 2) 1,4-dioxane, reflux, overnight

2: Et₃N / acetone / 0.17 h / -30 °C

3: NaN₃ / H₂O / 0.5 h / Ambient temperature

4: toluene / Heating

5: 95 percent / KOH / tetrahydrofuran; H₂O / 0 °C

6: 98 percent / Et₃N / CH₂Cl₂ / 0 °C

7: 1.) N₂O₄, 2.) NaOAc / 1) CCl₄, 0-5 deg C, 5 min; 2) CCl₄, 0-5 deg C, 30 min

8: 86 percent / petroleum ether / Heating

9: Na, NH₃ / dioxane / 0.17 h / -70 °C

10: 70 percent / pyridine / CH₂Cl₂ / 0.17 h / 0 °C

11: 1.) Et₃N, 2.) bis(dibenzylideneacetone)palladium⁽⁰⁾, triisopropyl phosphite / 1) THF, hexane, 60 deg C, 10-20 min; 2) THF, hexane, 60 deg C, 1-2 h; further reagent and solvent

12: 97 percent / Na, methanol / Ambient temperature

With pyridine; methanol; potassium hydroxide; sodium azide; triisopropyl phosphite; ammonia; sodium acetate; sodium; dinitrogen tetraoxide; triethylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; toluene; Petroleum ether;

DOI:10.1016/S0040-4020(97)10380-5

upstream raw materials:

(+/-)-4β-Hydroxymethyl-1β-cyclopent-2-ene

C-5'-O-trityl-2,3'-anhydrothymidine

methyl cis-(4-hydroxy-2-cyclopenten-1-yl)acetate

cis-4-Hydroxy-2-cyclopenten-1-methanol

Downstream raw materials:

(+/-)-1-<(1α,2β,4α)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-methyl-2,4-(1H,3H)pyrimidinedione

(+/-)-1-<(1α,2α,4α)-2-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-methyl-2,4(1H,3H)-pyrimidinedione