ChemicalBook CAS DataBase List 4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE

4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE synthesis

6synthesis methods

Product Name:4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE
CAS Number:182198-35-2
Molecular formula:C12H7ClN2S
Molecular Weight:246.72

7-phenyl-9-thia-2,4-diazabicyclo[4.3.0]nona-2,7,10-trien-5-one

35978-39-3
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$23.00/1g

4-CHLORO-5-PHENYLTHIENO[2,3-D]PYRIMIDINE

182198-35-2
57 suppliers
$45.00/250mg

Yield: 100%

Reaction Conditions:

with thionyl chloride;N,N-dimethyl-formamide at 80; for 4 h;Product distribution / selectivity;

Steps:

B.5
4-Hydroxyquinazoline (1.0 eq.) was suspended in thionylchloride (2 mL/mmol), three catalytic drops of DMF were added and the mixture was heated to 80°C for 4 h. Thionylchloride was removed in vacuum, toluene (0.5 mL/mmol) was added and removed again under reduced pressure. The remaining solid was dried at high vacuum over night, taken up in ethylene glycol (3 mL/mmol) and treated with 4-(N-Boc-amino)piperidine (1.4 eq.) and DIEA (1.0 eq.). The mixture was heated to 110° for 3 h. For Boc-removal, 4 M HCl/dioxane (3 mL/mmol) was added under cooling (ice bath) and the mixture was stirred at r.t. for 2 h. The solution was partitioned between 1.3 N aq. NaOH / brine (2:1, 20 mL/mmol) and CHCl₃ (4x10 mL/mmol). Combined organic phases were dried over MgSO₄ to give a yellow-brownish oily solid as crude product.; 1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine Synthesis followed SP5, using 2.3 mmol 5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one or 5-phenyl-thieno[2,3-d]pyrimidin-4-ol to give the title compound quantitatively, containing around 25% water even upon extensive drying in high vacuum.

References:

4SC AG EP1947103, 2008, A1 Location in patent:Page/Page column 18

35978-39-3
65 suppliers
$23.00/1g

182198-35-2
57 suppliers
$45.00/250mg

References

4815-36-5 Synthesis