4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine
• CAS No.: 16372-08-0
• Molecular Formula: C6H6ClN3
• Molecular Weight: 155.587
• Hs Code.: 2933990090
• Mol file: 16372-08-0.mol

Synonyms:5H-pyrrolo[2,3-d]pyrimidine, 4-chloro-6,7-dihydro-;

Chemical Property of 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Chemical Property:

• Melting Point: 158.5-160 °C
• Refractive Index: 1.592
• Boiling Point: 311.9 °C at 760 mmHg
• PKA: 11.69±0.20(Predicted)
• Flash Point: 142.5 °C
• PSA: 41.57000
• Density: 1.377 g/cm³
• LogP: 1.61130
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

4-Chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine is a pyrolopyrimidine derivative used in the preparation of the antibiotic tubercidin (7-deazadenosine). A pyrolopyrimidine derivative used in the preparation of the antibiotic tubercidin (7-deazadenosine).

Technology Process of 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

There total 6 articles about 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine 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: 52.0%

C6H7Cl2N3 (910399-87-0) → 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (16372-08-0)

Guidance literature:

C₆H₇Cl₂N₃; With potassium phosphate; In dimethyl sulfoxide; for 0.166667h;

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In dimethyl sulfoxide; at 110 ℃; for 1h;

DOI:10.1021/jm401625b

Reference yield:

(4,6-dihydroxy-pyrimidin-5-yl)-acetic acid methyl ester → 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (16372-08-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: trichlorophosphate; N,N-diethylaniline / 2 h / 130 °C

2.1: diisobutylaluminium hydride / diethyl ether; toluene / -78 - 20 °C

3.1: triethylamine / dichloromethane / 15 h / 0 - 20 °C

4.1: triethylamine / 1,2-dichloro-ethane / 15 h / 80 °C

5.1: trifluoroacetic acid / 15 h / Reflux

6.1: potassium phosphate / dimethyl sulfoxide / 0.17 h

6.2: 1 h / 110 °C

With potassium phosphate; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; N,N-diethylaniline; trichlorophosphate; In diethyl ether; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jm401625b

Reference yield:

methyl 2-(4,6-dichloropyrimidin-5-yl)acetate (171096-33-6) → 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (16372-08-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / diethyl ether; toluene / -78 - 20 °C

2.1: triethylamine / dichloromethane / 15 h / 0 - 20 °C

3.1: triethylamine / 1,2-dichloro-ethane / 15 h / 80 °C

4.1: trifluoroacetic acid / 15 h / Reflux

5.1: potassium phosphate / dimethyl sulfoxide / 0.17 h

5.2: 1 h / 110 °C

With potassium phosphate; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jm401625b

upstream raw materials:

methyl 2-(4,6-dichloropyrimidin-5-yl)acetate

2-(4,6-dichloropyrimidin-5-yl)ethanol

methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester

C₁₄H₁₅Cl₂N₃O

Downstream raw materials:

C₁₇H₁₅FN₄O₃

C₁₇H₁₅FN₄O₃

[2-[4-(6,7-dihydro-5H-pyrrolo[2.3-d]pyrimidin-4-yl)-piperazin-1-yl]-2-(4-trifluoromethylphenyl)-ethyl]-dimethylamine