2(1H)-Pyrimidinone, tetrahydro-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-, (4R,5R,6R)-

Base Information

• Chemical Name: 2(1H)-Pyrimidinone, tetrahydro-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-, (4R,5R,6R)-
• CAS No.: 189818-21-1
• Molecular Formula: C19H22N2O2
• Molecular Weight: 310.396
• Mol file: 189818-21-1.mol

Synonyms:

Chemical Property of 2(1H)-Pyrimidinone, tetrahydro-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-, (4R,5R,6R)-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2(1H)-Pyrimidinone, tetrahydro-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-, (4R,5R,6R)-

There total 17 articles about 2(1H)-Pyrimidinone, tetrahydro-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-, (4R,5R,6R)- 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:

Cbz-D-Phe (2448-45-5) → (4R,5R,6R)-tetrahydro-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone (189818-21-1)

Guidance literature:

Multi-step reaction with 12 steps

1: N-methylmorpholine / tetrahydrofuran / 0.33 h / -20 °C

2: tetrahydrofuran; dimethylformamide / 0.5 h

3: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

4: CeCl₃*7H₂O, NaBH₄ / methanol / 0.5 h / Ambient temperature

5: diisopropylethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 1.) CuCN / 1.) THF, a) -70 deg C, 20 min, b) 0 deg C, 30 min, 2.) THF, -70 deg C, 60 min

7: MCPBA / CH₂Cl₂ / 7 h / 0 °C

8: NaN₃, NH₄Cl / dimethylformamide; H₂O / a) 85 deg C, 3 h, b) RT, overnight

9: 90 percent / diisopropylamine / CH₂Cl₂ / Heating

10: H₂, AcOH / Pearlman's catalyst / ethyl acetate / 20 h / 2844.3 Torr

11: tetrahydrofuran / Ambient temperature

12: 20 mg / HCl / methanol / 5 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; hydrogen; ammonium chloride; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm970081i

Reference yield:

(4R,5S,6R)-tetrahydro-5-(hydroxy)-4-(β-styrene)-6-(phenylmethyl)-2(1H)-pyrimidinone (210635-14-6) → (4R,5R,6R)-tetrahydro-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone (189818-21-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; for 3h; under 2585.7 Torr; Ambient temperature;

DOI:10.1021/jo980533e

Reference yield:

Acetic acid (4R,5S,6S,7R)-4,7-dibenzyl-6-hydroxy-2-oxo-[1,3]diazepan-5-yl ester (179894-02-1) → (4R,5R,6R)-tetrahydro-5-hydroxy-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone (189818-21-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.9 g / DAST / CH₂Cl₂ / 0.5 h / 0 °C

2: 900 mg / HBr gas / dioxane / 0.33 h / Ambient temperature

3: KOH / methanol / Ambient temperature

4: 6.3 g / H₂ / 10 percent Pd/C / tetrahydrofuran; methanol / 3 h / 2585.74 Torr / Ambient temperature

With potassium hydroxide; hydrogen bromide; hydrogen; 4,4'-diaminostilbene-2,2'-disulfonic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jm9803626

upstream raw materials:

(4R,5R,6R)-tetrahydro-5-O-[(2-methoxyethoxy)methyl]-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

(4R,5S,6R)-tetrahydro-5-(hydroxy)-4-(β-styrene)-6-(phenylmethyl)-2(1H)-pyrimidinone

(4R,5R,6R)-tetrahydro-5-(acetyloxy)-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

Acetic acid (4R,5S,6S,7R)-4,7-dibenzyl-6-hydroxy-2-oxo-[1,3]diazepan-5-yl ester

Downstream raw materials:

(4R,5R,6R)-tetrahydro-5-(tetrahydropyran-2-yl-oxy)-4-(2-phenylethyl)-6-(phenylmethyl)-2(1H)-pyrimidinone

(4R,5R,6R)-4-Benzyl-6-phenethyl-5-(tetrahydro-pyran-2-yloxy)-1,3-bis-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-ylmethyl]-tetrahydro-pyrimidin-2-one

(4R,5R,6R)-6-Benzyl-1-(3-nitro-benzyl)-4-phenethyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyrimidin-2-one

(4R,5S,6R)-4-Benzyl-1-(3-nitro-benzyl)-6-phenethyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyrimidin-2-one