| Identification | Back Directory | [Name]
N-(4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDIN-2-YL)-2,2-DIMETHYLPROPIONAMIDE | [CAS]
149765-15-1 | [Synonyms]
N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)
N2-Pivaloyl-4-chloro-7H-pyrrolo[2,3-d]pyriMidine
N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide
N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpro...
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-DIMETHYLPROPIONAMIDE
PropanaMide, N-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-2-yl)-2,2-diMethyl-
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 | [Molecular Formula]
C11H13ClN4O | [MDL Number]
MFCD11109809 | [MOL File]
149765-15-1.mol | [Molecular Weight]
252.7 |
| Hazard Information | Back Directory | [Synthesis]
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 |
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