2-amino-9-[(1S,3R)-3-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one

Base Information

• Chemical Name: 2-amino-9-[(1S,3R)-3-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one
• CAS No.: 112915-00-1
• Molecular Formula: C₁₁H₁₅N₅O₂
• Molecular Weight: 249.272
• Mol file: 112915-00-1.mol

Synonyms:6H-Purin-6-one,2-amino-1,9-dihydro-9-[3-(hydroxymethyl)cyclopentyl]-, cis- (9CI);6H-Purin-6-one, 2-amino-1,9-dihydro-9-[3-(hydroxymethyl)cyclopentyl]-, cis-(?à)-; NSC 615813

Chemical Property of 2-amino-9-[(1S,3R)-3-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one

Chemical Property:

• Vapor Pressure: 8.59E-15mmHg at 25°C
• Boiling Point: 590.6°C at 760 mmHg
• Flash Point: 311°C
• Density: 1.77g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-amino-9-[(1S,3R)-3-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-one

There total 7 articles about 2-amino-9-[(1S,3R)-3-(hydroxymethyl)cyclopentyl]-3,9-dihydro-6H-purin-6-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: 77.0%

(+/-)-cis-<3-(2-amino-6-chloro-9H-purin-9-yl)cyclopentyl>carbinol (118237-86-8,2022943-79-7) → (+/-)-cis-2-amino-1,9-dihydro-9-<3-(hydroxymethyl)cyclopent-1-yl>-6H-purin-6-one (112915-00-1)

Guidance literature:

With sodium hydroxide; for 5h; Heating;

DOI:10.1021/jm00163a004

Reference yield:

Acetic acid 4-acetylamino-cyclopent-2-enylmethyl ester (61865-50-7,86252-77-9) → (+/-)-cis-2-amino-1,9-dihydro-9-<3-(hydroxymethyl)cyclopent-1-yl>-6H-purin-6-one (112915-00-1)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / 10percent Pd/C / ethanol

2: 0.5 N aq. barium hydroxide / Heating; overnight

3: Et₃N / butan-1-ol / 48 h / Heating

4: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight

5: 69 percent / Zn, acetic acid / H₂O; ethanol / 3 h / Heating

6: 73 percent / 12 N HCl / overnight

7: 77 percent / 0.33 N aq. NaOH / 5 h / Heating

With hydrogenchloride; barium dihydroxide; sodium hydroxide; hydrogen; sodium acetate; acetic acid; triethylamine; zinc; sodium nitrite; palladium on activated charcoal; In ethanol; water; butan-1-ol;

DOI:10.1021/jm00163a004

Reference yield:

3-aminocyclopentyl-1-methanol (123288-54-0,1110772-11-6) → (+/-)-cis-2-amino-1,9-dihydro-9-<3-(hydroxymethyl)cyclopent-1-yl>-6H-purin-6-one (112915-00-1)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / butan-1-ol / 48 h / Heating

2: 1.) 3 N HCl, sodium nitrite, 2.) sodium acetate trihydrate / 1.) water, 2.) acetic acid, water, RT, overnight

3: 69 percent / Zn, acetic acid / H₂O; ethanol / 3 h / Heating

4: 73 percent / 12 N HCl / overnight

5: 77 percent / 0.33 N aq. NaOH / 5 h / Heating

With hydrogenchloride; sodium hydroxide; sodium acetate; acetic acid; triethylamine; zinc; sodium nitrite; In ethanol; water; butan-1-ol;

DOI:10.1021/jm00163a004

upstream raw materials:

(+/-)-cis-<3-(2-amino-6-chloro-9H-purin-9-yl)cyclopentyl>carbinol

3-aminocyclopentyl-1-methanol

Acetic acid 3-acetylamino-cyclopentylmethyl ester

Acetic acid 4-acetylamino-cyclopent-2-enylmethyl ester