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252723-16-3

252723-16-3 Structure

252723-16-3 Structure
IdentificationBack Directory
[Name]

7-Benzenesulfonyl-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyri midine
[CAS]

252723-16-3
[Synonyms]

4-Chloro-6-methyl-7-(phenylsulfonyl)pyrrolo[2,3-d]pyrimidine
7-Benzenesulfonyl-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyri midine
4-Chloro-6-methyl-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine
7H-Pyrrolo[2,3-d]pyrimidine, 4-chloro-6-methyl-7-(phenylsulfonyl)-
[Molecular Formula]

C13H10ClN3O2S
[MDL Number]

MFCD12407798
[MOL File]

252723-16-3.mol
[Molecular Weight]

307.76
Chemical PropertiesBack Directory
[Boiling point ]

511.4±60.0 °C(Predicted)
[density ]

1.49±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[pka]

1.93±0.30(Predicted)
Hazard InformationBack Directory
[Synthesis]

4-CHLORO-7-(PHENYLSULFONYL)-7H-PYRROLO[2,3-D]PYRIMIDINE

186519-89-1

Iodomethane

74-88-4

7-Benzenesulfonyl-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyri midine

252723-16-3

Step 2: 4-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (3 g, 12.6 mmol, 1.0 eq.) and N,N,N',N'-tetramethylethylenediamine (TMEDA) (3.0 mL, 18.9 mmol, 1.5 eq.) were dissolved in tetrahydrofuran (THF) (120 mL), and cooled to -78 °C. The reaction was purified by adding n-butyl lithium (n-BuLi) (7.5 mL, 18.9 mmol, 1.5 eq.). Under stirring, n-butyllithium (n-BuLi) (7.5 mL, 18.9 mmol, 1.5 eq.) was slowly added. after 3 min, iodomethane (C3/4I) (3.7 mL, 59.2 mmol, 4.7 eq.) was added. The reaction mixture was kept stirred at -78 °C for 3 h, followed by a slow warming to room temperature over 1 h. The reaction was completed by the addition of iodomethane (C3/4I). Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride (NH4Cl) solution (10 mL). Extraction was performed by adding ethyl acetate (EtOAc) (200 mL) and water (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 7-benzenesulfonyl-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine as a brown solid (6.7 g, 90% yield).

[References]

[1] Patent: WO2012/158795, 2012, A1. Location in patent: Page/Page column 101-102
[2] Patent: WO2012/158764, 2012, A1. Location in patent: Page/Page column 115
[3] Patent: WO2013/191965, 2013, A1. Location in patent: Page/Page column 191
[4] Patent: WO2014/22569, 2014, A1. Location in patent: Page/Page column 96
[5] Patent: US8673925, 2014, B1. Location in patent: Page/Page column 241
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