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

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N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide manufacturers
N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide Basic information
Product Name:N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide
Synonyms:PropanaMide, N-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-2-yl)-2,2-diMethyl-;N2-Pivaloyl-4-chloro-7H-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)pivalamide;N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl);N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl propanamide, N2-Pivaloyl-2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidine;N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpro...;N2-Pivaloyl-2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
CAS:149765-15-1
MF:C11H13ClN4O
MW:252.7
EINECS:
Product Categories:
Mol File:149765-15-1.mol
N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide Structure
N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide Chemical Properties
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
Safety Information
MSDS Information
N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide Usage And Synthesis
Synthesis
Propanamide, N-(4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-

137281-08-4

N-(4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDIN-2-YL)-2,2-DIMETHYLPROPIONAMIDE

149765-15-1

Step 3. Synthesis of N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide N-(4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide (210 g, 0.90 mol), phosphorus oxychloride (POCl3, 828 g, 5.40 mol, 503 mL, 6.0 equiv), benzyltriethylammonium chloride (411 g, 1.80 mol), N,N- dimethylaniline (220 g, 231 mL, 1.80 mol) and acetonitrile (2.0 L) were mixed and heated to reflux for 40-60 min, the reaction was monitored by HPLC. Upon completion of the reaction, the solvent was evaporated on a rotary evaporator and the residue was carefully (note: exothermic and corrosive) added slowly to ice water (16 L). The pH was adjusted to 7 with solid sodium hydroxide (NaOH) and the resulting precipitate was collected by filtration. The precipitate was dried to give N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide (159 g, 70% yield, 100% HPLC purity). Retention time (tR): 5.37 min. 1H-NMR (DMSO-d6) δ 12.35 (broad single peak, 1H), 10.06 (broad single peak, 1H), 7.54 (quadruple peak, 1H), 6.52 (quadruple peak, 1H), 1.25 (single peak, 9H).

References[1] Patent: US2006/223797, 2006, A1. Location in patent: Page/Page column 83-84
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7786 - 7795
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 4, p. 591 - 600
N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide Preparation Products And Raw materials
Raw materialsPropanamide, N-(4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl--->trichlorophosphate-->Benzyltriethylammonium chloride-->N,N-Dimethylaniline-->Acetonitrile
Tag:N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide(149765-15-1) Related Product Information
N-(4-Chloro-5-fluoro-3-iodopyridin-2-yl)pivalamide N-[4-(4-Amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-methylesulfonamide N2-Pivaloyl-4-chloro-5-cyano-7H-pyrrolo[2,3-d]pyriMidine Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl- N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide 2-Amino-4-chloropyrrolo[2,3-d]pyrimidine