N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide

Base Information

• Chemical Name: N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide
• CAS No.: 149765-16-2
• Molecular Formula: C11H12 Cl I N4 O
• Molecular Weight: 378.6
• DSSTox Substance ID: DTXSID40573208
• Nikkaji Number: J2.110.190G
• Wikidata: Q82461824
• Mol file: 149765-16-2.mol

Synonyms:149765-16-2;N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide;N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide;N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide;Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-;MFCD11109808;N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyriMidin-2-yl)-2,2-diMethyl propanaMide;C11H12ClIN4O;KZDHRXDFCHHFEJ-UHFFFAOYSA-N;SCHEMBL312171;AMY753;DTXSID40573208;BCP10652;AKOS015850395;CS-W023094;N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propanamide;DS-10572;W-205695;4-Chloro-5-iodo-2-trimethylacetamido-pyrrolo[2,3-d]pyrimidine;Tert-butylN-[2-amino-2-(3,4-dimethoxyphenyl)Ethyl]carbamate;N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide

Chemical Property of N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide

Chemical Property:

• Melting Point: 240 °C(Solv: methanol (67-56-1))
• PKA: 5.97±0.40(Predicted)
• PSA: 70.67000
• Density: 1.847g/cm³
• LogP: 3.27350
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 377.97444
• Heavy Atom Count: 18
• Complexity: 336

Purity/Quality:

97% ^*data from raw suppliers

N-(4-Chloro-5-iodo-7h-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C(=O)NC1=NC2=C(C(=CN2)I)C(=N1)Cl

Technology Process of N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide

There total 8 articles about N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide 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: 93.0%

N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-15-1) → N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-16-2)

Guidance literature:

With N-iodo-succinimide; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201904623

Reference yield:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / pyridine / 5 h / 20 °C

2: 85 percent / N-iodosuccinimide / CH₂Cl₂ / 5 h / 40 °C

With pyridine; N-iodo-succinimide; In dichloromethane;

DOI:10.1055/s-2004-822382

Reference yield:

2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (7355-55-7) → N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-16-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / POCl₃ / 2 h / Heating

2: 73 percent / pyridine / 0.5 h / Ambient temperature

3: 83 percent / N-iodosuccinimide / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; N-iodo-succinimide; trichlorophosphate; In tetrahydrofuran;

DOI:10.3987/COM-92-S(T)65

upstream raw materials:

N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide

pivaloyl chloride

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide

Downstream raw materials:

chloro-7-[2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodo-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine

4-chloro-5-iodo-2-pivaloylamino-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

C₁₈H₁₈ClIN₄O

4-chloro-5-iodo-2-(pivaloylamino)-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine