ChemicalBook CAS DataBase List PF-06447475

PF-06447475 synthesis

4synthesis methods

Product Name:PF-06447475
CAS Number:1527473-33-1
Molecular formula:C17H15N5O
Molecular Weight:305.33

110-91-8 Synthesis

110-91-8
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Benzonitrile, 3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-

1527475-89-3
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1527473-33-1
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$25.00/1mg

Yield:1527473-33-1 26%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in butan-1-ol for 3 h;Reflux;

Steps:

4.4 Step 4. Synthesis of 3-[4-(morpholin-4-yl)-7H-pyrrolo[2, 3-d]pyrimidin-5-yl]benzonitrile(4).
Morpholine (871 mg, 10 mmol) and N,N-diisopropylethylamine (2.6 g, 20 mmol) were added to a solution of 3-(4-ch loro-7H-pyrrolo[2, 3-d]pyrim idin-5-yl)benzonitrile (C14) (2.5 g, 9.8 mmol) in n-butanol (100 mL), and the reaction mixture was heated at reflux for 3 hours. Solvents were removed in vacuo and the residue was purified using chromatography on silica gel (Eluent: 1:1 ethyl acetate petroleum ether). Subsequent recrystallization from ethyl acetate and tert-butyl methyl ether afforded the product as a white solid. Yield: 770 mg, 2.52 mmol, 26%. LCMS m/z 306.0 [M+H]. 1H NMR (400MHz, DMSO-d6) 12.34 (br s, 1H), 8.41 (s, 1H), 7.99-8.02 (m, 1H), 7.89 (br d, J=8 Hz,1 H), 7.76 (br d, J=7.5 Hz, 1 H), 7.71 (s, 1 H), 7.68 (dd, J=7.8, 7.8 Hz, 1 H), 3.44-3.50 (m,4H), 3.11-3.17 (m, 4H).

References:

PFIZER INC.;GALATSIS, Paul;HAYWARD, Matthew Merrill;HENDERSON, Jaclyn;KORMOS, Bethany Lyn;KURUMBAIL, Ravi G;STEPAN, Antonia Friederike;VERHOEST, Patrick Robert;WAGER, Travis T.;ZHANG, Lei WO2014/1973, 2014, A1 Location in patent:Page/Page column 56; 57; 58

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