(R)-5-(2-((Tert-Butyldimethylsilyl)Oxy)Ethyl)-4-Chloro-6,7-Dihydro-5H-Cyclopenta[4,5]Thieno[2,3-D]Pyrimidine synthesis

6synthesis methods

Product Name:(R)-5-(2-((Tert-Butyldimethylsilyl)Oxy)Ethyl)-4-Chloro-6,7-Dihydro-5H-Cyclopenta[4,5]Thieno[2,3-D]Pyrimidine
CAS Number:1388894-05-0
Molecular formula:C17H25ClN2OSSi
Molecular Weight:369

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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18162-48-6 Synthesis

18162-48-6
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(R)-5-(2-((Tert-Butyldimethylsilyl)Oxy)Ethyl)-4-Chloro-6,7-Dihydro-5H-Cyclopenta[4,5]Thieno[2,3-D]Pyrimidine

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Yield: 96%

Reaction Conditions:

with 1H-imidazole in N,N-dimethyl-formamide at 20; for 2 h;Inert atmosphere;

Steps:

25
Example 25: Synthesis of Intermediate Hb.Fb Hb (21b)[00627] Intermediate Fb (1.3 g, 5.10 mmol, 1.00 equiv) was treated with imidazole (500 mg, 7.44 mmol, 1.40 equiv) and TBDMSCl (920 mg, 6.10 mmol, 1.20 equiv) in distilled DMF (10 mL) for 2 h at room temperature under nitrogen. The reaction was then quenched with water and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1 :5) and purified to give (-?R)-3-[2-[(½ri-butyldimethylsilyl)oxy]ethyl]-12-chloro-7-thia-9, l l- diazatricyclo[6.4.0.0[2,6]]dodeca-l(8),2(6),9,l l-tetraene (Hb, 1.8 g, 96%) as a yellow oil.

References:

NIMBUS IRIS, INC.;ROMERO, Donna L.;WESSEL, Matthew David;ROBINSON, Shaughnessy;GREENWOOD, Jeremy Robert;WATTS, Karl Shawn;FRYE, Leah Lynn;HARRIMAN, Geraldine C.;CORIN, Alan Franklin;MASSE, Craig WO2012/97013, 2012, A1 Location in patent:Page/Page column 277

20826-94-2 Synthesis

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References

diethyl 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3,4-dicarboxylate

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References

1388893-76-2 Synthesis

ethyl 4-hydroxy-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine-5-carboxylate

1388893-76-2
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1388894-05-0
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References

ethyl 2-(4-chloro-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-5-yl)acetate

1388893-77-3
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1388894-05-0
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References