2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one

Base Information

• Chemical Name: 2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one
• CAS No.: 191600-64-3
• Molecular Formula: C₁₈H₂₀N₄O₃
• Molecular Weight: 340.382
• Mol file: 191600-64-3.mol

Synonyms:2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one

Chemical Property of 2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one

There total 8 articles about 2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one 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: 80.0%

2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]-4-chloropyrrolo[2,3-d]pyrimidine (191600-62-1) → 2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one (191600-64-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 24h; Heating;

DOI:10.1080/07328319708001366

Reference yield:

3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (3396-71-2) → 2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one (191600-64-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / NaH / dimethylformamide / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

2: 1.) IR-120(H⁺), 2.) Et₃SiH, BF₃*Et₂O / 1.) CH₃OH, reflux, 16 h, 2.) CH₂Cl₂, room temperature, 40 h

3: 98 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

4: 93 percent / NaN₃ / dimethylsulfoxide / 5 h / 100 °C

5: 88 percent / H₂ / PtO₂ / ethanol / 24 h / 760 Torr / Ambient temperature

6: 1.) Et₃N, 2.) aq. HCl / 1.) 2-ethoxyethane, reflux, 7 h, 2.) dioxane, room temperature, 3 d

7: 80 percent / NaOH / dioxane; H₂O / 24 h / Heating

With hydrogenchloride; triethylsilane; sodium hydroxide; sodium azide; IR-120(H⁺); boron trifluoride diethyl etherate; hydrogen; sodium hydride; triethylamine; platinum(IV) oxide; In 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1080/07328319708001366

Reference yield:

benzyl bromide (100-39-0) → 2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]pyrrolo[2,3-d]pyrimidin-4(3H)-one (191600-64-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / NaH / dimethylformamide / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

2: 1.) IR-120(H⁺), 2.) Et₃SiH, BF₃*Et₂O / 1.) CH₃OH, reflux, 16 h, 2.) CH₂Cl₂, room temperature, 40 h

3: 98 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

4: 93 percent / NaN₃ / dimethylsulfoxide / 5 h / 100 °C

5: 88 percent / H₂ / PtO₂ / ethanol / 24 h / 760 Torr / Ambient temperature

6: 1.) Et₃N, 2.) aq. HCl / 1.) 2-ethoxyethane, reflux, 7 h, 2.) dioxane, room temperature, 3 d

7: 80 percent / NaOH / dioxane; H₂O / 24 h / Heating

With hydrogenchloride; triethylsilane; sodium hydroxide; sodium azide; IR-120(H⁺); boron trifluoride diethyl etherate; hydrogen; sodium hydride; triethylamine; platinum(IV) oxide; In 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1080/07328319708001366

upstream raw materials:

2-amino-7-[(2S,4S)-(2-benzyloxymethyl)-tetrahydrofuran-4-yl]-4-chloropyrrolo[2,3-d]pyrimidine

3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

benzyl bromide

(3αR,5S,6αR)-5-(benzyloxymethyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole