| Identification | Back Directory | [Name]
6-bromo-4-chlorothieno[3,2-d]pyrimidine | [CAS]
225385-03-5 | [Synonyms]
CML-008
6-bromo-4-chlorothieno[3,2-d]pyrimidine
4-Chloro-6-bromothieno[3,2-d]pyrimidine
Thieno[3,2-d]pyrimidine,6-bromo-4-chloro-
6-broMo-4-chlorothieno[3,2-d]pyriMidine hcl
6-bromo-4-chlorothieno[3,2-d]pyrimidine ISO 9001：2015 REACH | [EINECS(EC#)]
635-520-2 | [Molecular Formula]
C6H2BrClN2S | [MDL Number]
MFCD09746330 | [MOL File]
225385-03-5.mol | [Molecular Weight]
249.52 |
| Chemical Properties | Back Directory | [Boiling point ]
345.5±37.0 °C(Predicted) | [density ]
1.955 | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
solid | [pka]
-0.19±0.40(Predicted) | [Appearance]
Off-white to light yellow Solid | [InChI]
InChI=1S/C6H2BrClN2S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H | [InChIKey]
RJKAKJGOZXERRE-UHFFFAOYSA-N | [SMILES]
C1=NC(Cl)=C2SC(Br)=CC2=N1 |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
45 | [RIDADR ]
UN 2811 6.1 / PGIII | [HazardClass ]
IRRITANT | [HS Code ]
2934999090 |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 6-bromo-4-chlorothieno[3,2-d]pyrimidines from 4-chlorothieno[3,2-d]pyrimidines: to dry 200 mL of tetrahydrofuran was added lithium diisopropylamine (25 mL, 61.54 mmol), and the reaction system was cooled to -78 °C. Subsequently, 4-chlorothieno[3,2-d] Pyrimidine (5 g, 39.30 mmol) was slowly added dropwise to the above mixture. After 20 min of reaction, 1,2-dibromo-1,1,2,2-tetrafluoroethane (11.45 g, 35.17 mmol) was slowly added. Stirring was continued at -78°C for 20 minutes, then gradually warmed to room temperature and continued for 2 hours. Upon completion of the reaction, water was added to the mixture and extracted with chloroform (3 x 300 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the mixture was developed with 200 mL of hexane to afford 6-bromo-4-chlorothieno[3,2-d]pyrimidine (6.5 g, 89.2% yield) as a dark brown solid. The product was characterized by 1H-NMR (400 MHz, CDCl3): δ 8.94 (s, 1H), 7.62 (s, 1H); LC-MS showed molecular ion peaks of 249 and 251 (MH+). | [References]
[1] MedChemComm, 2015, vol. 6, # 2, p. 339 - 346
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[3] Patent: US2013/72482, 2013, A1. Location in patent: Paragraph 0211; 0218; 0219
[4] Patent: US2007/99941, 2007, A1. Location in patent: Page/Page column 15
[5] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 21 - 24 |
|
|