4-Chloro-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine synthesis
- Product Name:4-Chloro-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine
- CAS Number:208459-81-8
- Molecular formula:C12H8ClN3
- Molecular Weight:229.66
871671-45-3
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208459-81-8
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Yield:208459-81-8 47%
Reaction Conditions:
with trichlorophosphate in N,N-dimethyl-formamide at 120; for 1 h;
Steps:
Ex-1 4-Chloro-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine (A20)
5-Phenyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (A19) ( 1 .53 g, 7.25 mmol) was dissolved in (0644) POCI3 (36 mL, 7.2 mmol) and DMF (6.5 mL) and the reaction mixture was heated at 120°C for 1 h. The reaction mixture was evaporated to obtain a viscous oil. Ice was added to the residue and the residue was placed in an ice-bath. NH4OH (aq, 30% NH3) was added with continuous stirring and the residue basified to pH10 then extracted with DCM (3 x 200 mL). The organic layer was passed through a phase separatorand evaporated to dryness. A precipitate was observed in both the aqueous layer and phase separation cartridge which was filtered and found to contain the desired product. This precipitate was combined with the evaporated filtrate. The crude compound was purified by silica gel column chromatography eluting with 15% - 35% EtOAc//'so-hexane to obtain 4- chloro-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine (A20) as an off-white solid (789 mg, 47%); LC-MS. Rt 3.01 min, AnalpH2_MeOH_4min(1 ); (ESI+) m/z 230.3, 232.3 [M+H]+; NMR (400 MHz, DMSO-c/6): δ 12.83-12.79 (br s, 1 H), 8.63 (s, 1 H), 7.79 (s, 1 H), 7.55 (m, 2H), 7.44 (m, 2H), 7.36 (m, 1 H).
References:
WO2019/73253,2019,A1 Location in patent:Paragraph 00226
54153-51-4
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208459-81-8
12 suppliers
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