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[ CAS No. 1276110-38-3 ] {[proInfo.proName]}

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Chemical Structure| 1276110-38-3
Chemical Structure| 1276110-38-3
Structure of 1276110-38-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1276110-38-3 ]

CAS No. :1276110-38-3 MDL No. :MFCD27987084
Formula : C15H21IN6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YQXAEBHPCJZKKX-SECBINFHSA-N
M.W : 444.27 Pubchem ID :58441419
Synonyms :

Safety of [ 1276110-38-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1276110-38-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1276110-38-3 ]
  • Downstream synthetic route of [ 1276110-38-3 ]

[ 1276110-38-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1276110-38-3 ]
  • [ 51067-38-0 ]
  • [ 1022150-11-3 ]
YieldReaction ConditionsOperation in experiment
64% With sodium carbonate In 1,4-dioxane; water at 90℃; for 24 h; Inert atmosphere Step 4A mixture of (R)-tert-butyl 3-[4-amino-3-iodo-lH-pyrazolo[3,4-d]pyrimidin-l- yl]piperidine-l-carboxylate (1 g, 2.25 mmol, 1 .00 equiv), (4-phenoxyphenyl)boronic acid (530 mg, 2.48 mmol, 1.10 equiv), sodium carbonate (480 mg, 4.53 mmol, 2.01 equiv) and tetrakis( triphenylphosphine)palladium (78 mg, 0.07 mmol, 0.03 equiv) in ,4-dioxane (60 mL) and water (15 mL) was stirred under nitrogen at 90°C for 24 h. The reaction mixture was cooled to room temperature and then concentrated under vacuum. The residue was dissolved in 500 mL of dichloromethane. The resulting solution was washed with 200 mL of water, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (100/1) to give 700 mg (64percent) of (R)-tert-butyl 3-[4-amino-3-(4-phenoxyphenyl)-lH-pyrazolo[3,4-d]pyrimidin-l- yl]piperidine-l-carboxylate as a yellow solid.
64% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 24 h; Inert atmosphere A mixture of (R)-tert-butyl 3[4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (1 g, 2.2.5 mmol, 1.00 equiv), (4-phenoxyphenyl)boronic acid (530 mg, 2.48 mmol, 1.10 equiv), sodium carbonate (480 mg, 4.53 mmol, 2.01 equiv) and tetrakis(triphenyiphosphine)palladium (78 mg, 0.07 mmol, 0.03 equiv) in 1,4-dioxane (60 mL) and water (15 mL) was stirred under nitrogen at 90°C for 24 h. The reaction mixture was cooled to room temperature and then concentrated under vacuum. The residue was dissolved in 500 mL of dichloromethane. The resulting solution was washed with 200 mL of water, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethauefmethanol (100/1) to give 700 mg (64percent) of (R)ert-butyl 1H-pyrazolo[3,4-d]pyrimidin-1-yi]piperidine-1-carboxylate as a yellow solid.
64% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 24 h; Inert atmosphere Step 4. A mixture of tert-butyl 3-[4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (1 g, 2.25 mmol, 1.00 equiv), (4-phenoxyphenyl)boronic acid (530 mg, 2.48 mmol, 1.10 equiv), sodium carbonate (480 mg, 4.53 mmol, 2.01 equiv) and tetrakis(triphenylphosphine)palladium (78 mg, 0.07 mmol, 0.03 equiv) in 1,4-dioxane (60 mL) and water (15 mL) was stirred under nitrogen at 90°C for 24 h. The reaction mixture was cooled to room temperature and then concentrated under vacuum. The residue was dissolved in 500 mL of dichloromethane. The resulting solution was washed with 200 mL of water, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (100/1) to give 700 mg (64percent) of tert-butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate as a yellow solid.
64% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 24 h; Inert atmosphere Step 4
A mixture of tert-butyl 3-[4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (1 g, 2.25 mmol, 1.00 equiv), (4-phenoxyphenyl)boronic acid (530 mg, 2.48 mmol, 1.10 equiv), sodium carbonate (480 mg, 4.53 mmol, 2.01 equiv) and tetrakis(triphenylphosphine)palladium (78 mg, 0.07 mmol, 0.03 equiv) in 1,4-dioxane (60 mL) and water (15 mL) was stirred under nitrogen at 90° C. for 24 h.
The reaction mixture was cooled to room temperature and then concentrated under vacuum.
The residue was dissolved in 500 mL of dichloromethane.
The resulting solution was washed with 200 mL of water, dried over anhydrous sodium sulfate and concentrated under vacuum.
The residue was purified on a silica gel column eluted with dichloromethane/methanol (100/1) to give 700 mg (64percent) of tert-butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate as a yellow solid.
60% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere (R) -1-Boc-3- (4-amino-3-iodo-1H-pyrazolo [3,4-D] pyrimidin-1-yl) piperidine (12.8G, 29 mmol),4-phenoxyphenylboronic acid (6.8 g, 32 mmol),PdCl2 (dppf) (0.5 g, 0.69 mmol),Sodium carbonate (6.1 g, 58 mmol),1,4-dioxane (160 ml) and water (40 ml) were added and the mixture was heated to 80 ° C overnight.After confirming the completion of the reaction,Filter, spin dry,Add water, extract with ethyl acetate, dry,The product was purified by column chromatography (8.5 g, yield 60percent).

Reference: [1] Patent: WO2012/158795, 2012, A1, . Location in patent: Page/Page column 76
[2] Patent: WO2013/191965, 2013, A1, . Location in patent: Page/Page column 156
[3] Patent: WO2014/22569, 2014, A1, . Location in patent: Page/Page column 50
[4] Patent: US8673925, 2014, B1, . Location in patent: Page/Page column 201
[5] Patent: CN106146511, 2016, A, . Location in patent: Paragraph 0150; 0151; 0152
[6] Patent: WO2016/151438, 2016, A1, . Location in patent: Page/Page column 12-13
  • 2
  • [ 101-55-3 ]
  • [ 1276110-38-3 ]
  • [ 1022150-11-3 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With palladium dichloro <1,1'-bis(diphenylphosphino)ferrocene>; potassium acetate In 1,4-dioxane at 100℃; for 5 h;
Stage #2: at 100℃; for 22 h;
4-Bromodiphenyl ether (X = Br) (3.74 g, 15 mmol) was dissolved in 1,4-dioxane (50 ml)Addition of pinacol diboronate(4.52 g, 18 mmol),Potassium acetate (1.78 g, 18 mmol).Then, the catalyst [1,1'-bis (diphenylPhosphine) ferrocene] palladium dichloride [Pd (dppf) 2Cl2] (1.5 mmol, 1.11 g).With stirring, heated to 100 ° C, the reaction 5h (TLCDetection of raw materials disappear).Then, Intermediate (14) (4.44 g, 10 mmol) was added, and the reaction was maintained at 100 ° C for 22 hours14 disappears).Then, after distilling off the organic solvent, Intermediate (9) (yellow solid, 3.41 g, yield 70percent, chemical purity and optical purity> = 99percent) was obtained.
Reference: [1] Patent: CN104557945, 2017, B, . Location in patent: Paragraph 0055-0057; 0059-0062; 0063-0068
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