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

Base Information

• Chemical Name: N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide
• CAS No.: 149765-15-1
• Molecular Formula: C11H13ClN4O
• Molecular Weight: 252.703
• DSSTox Substance ID: DTXSID70465501
• Wikidata: Q82291495
• Mol file: 149765-15-1.mol

Synonyms:149765-15-1;N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide;N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide;N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide;MFCD11109809;N-{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl}-2,2-dimethylpropanamide;Propanamide, N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-;HNBVXLCVUIJCSK-UHFFFAOYSA-N;SCHEMBL311465;AMY752;DTXSID70465501;AKOS015850394;CS-W006652;DS-0426;SY104925;FT-0697722;A21578;2-pivaloylamino-4-chloro-pyrrolo[2,3-d]pyrimidine;4-Chloro-2-trimethylacetamido-pyrrolo[2.3-d]pyrimidine;N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propanamide;N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide;N-(4-Chloro-7H-pyrrolo[2 pound not3-d]pyrimidin-2-yl)-2 pound not2-dimethylpropionamide

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

Chemical Property:

• Refractive Index: 1.663
• PSA: 70.67000
• Density: 1.381 g/cm³
• LogP: 2.66890
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 252.0777887
• Heavy Atom Count: 17
• Complexity: 304

Purity/Quality:

97% ^*data from raw suppliers

N-(4-Chloro-7H-Pyrrolo[2,3-D]Pyrimidin-2-Yl)-2,2-Dimethylpropionamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 5 articles about N-(4-Chloro-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: 90.0%

pivaloyl chloride (3282-30-2) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-15-1)

Guidance literature:

With pyridine; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201904623

Reference yield: 70.0%

N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide (137281-08-4) → N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-15-1)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; N,N-dimethyl-aniline; trichlorophosphate; In acetonitrile; for 0.666667 - 1h; Heating / reflux;

Reference yield:

2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (7355-55-7) → N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (149765-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / POCl₃ / 2 h / Heating

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

With pyridine; trichlorophosphate;

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

upstream raw materials:

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

2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Downstream raw materials:

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

4,5-dichloro-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine

5-bromo-4-chloro-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine

4-chloro-5-fluoro-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine