| Identification | Back Directory | [Name]
2-Chlorothieno[3,2-d]pyrimidine | [CAS]
1119280-68-0 | [Synonyms]
2-Chlorothieno[3,2-d]pyrimidine
Thieno[3,2-d]pyrimidine, 2-chloro-
2-Chlorothieno[3,2-d]pyrimidine ISO 9001：2015 REACH | [EINECS(EC#)]
200-589-5 | [Molecular Formula]
C6H3ClN2S | [MDL Number]
MFCD12406127 | [MOL File]
1119280-68-0.mol | [Molecular Weight]
170.62 |
| Chemical Properties | Back Directory | [Melting point ]
165-166℃ | [density ]
1.531 | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
solid | [pka]
-0.06±0.40(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C6H3ClN2S/c7-6-8-3-5-4(9-6)1-2-10-5/h1-3H | [InChIKey]
QKRVOGZPQVCVPZ-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=C2SC=CC2=N1 |
| Hazard Information | Back Directory | [Synthesis]
GENERAL STEPS: 2,4-Dichlorothieno[3,2-d]pyrimidine (19 g, 58 mmol) was dissolved in a solvent mixture of ethanol (25 mL) and ethyl acetate (25 mL). To this solution was added sodium bicarbonate (1.1 g, 13.1 mmol) followed by 10% palladium carbon catalyst (0.206 g). The reaction mixture was stirred under hydrogen atmosphere for 5 h. The reaction progress was monitored by liquid chromatography-mass spectrometry (LC-MS) to confirm the formation of 2-chlorothieno[3,2-d]pyrimidine. Upon completion of the reaction, the mixture was filtered through diatomaceous earth to remove the catalyst and the filtrate was concentrated under reduced pressure to afford the off-white solid product 2-chlorothieno[3,2-d]pyrimidine (0.990 g, quantitative yield). The structure of the product was confirmed by 1H NMR (CDCl3): δ 9.17 (s, 1H), 8.16-8.12 (d, 1H), 7.55-7.51 (d, 1H). | [References]
[1] Patent: WO2011/79231, 2011, A1. Location in patent: Page/Page column 82
[2] Patent: WO2009/62258, 2009, A1. Location in patent: Page/Page column 91
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 2, p. 154 - 159
[4] Patent: WO2012/78859, 2012, A2. Location in patent: Page/Page column 59
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2113 - 2122 |
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