[ CAS No. 53636-15-0 ] {[proInfo.proName]}

Name: 53636-15-0|(2R)-1-(Dimethylamino)propan-2-ol|95%
Brand: Ambeed
SKU: A1063716
Price: 34.0 USD
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Quality Control of [ 53636-15-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 53636-15-0 ]

CAS No. :	53636-15-0	MDL No. :	MFCD00065951
Formula :	C₅H₁₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NCXUNZWLEYGQAH-RXMQYKEDSA-N
M.W :	103.16	Pubchem ID :	7057913
Synonyms :

Safety of [ 53636-15-0 ]

Signal Word:	Danger	Class:	3,8
Precautionary Statements:	P210-P280-P305+P351+P338-P310	UN#:	2924
Hazard Statements:	H225-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 53636-15-0 ]

* 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.

Downstream synthetic route of [ 53636-15-0 ]

[ 53636-15-0 ] Synthesis Path-Downstream 1~45

1
[ 108-16-7 ]
[ 87-69-4 ]
[ 53636-15-0 ]

Reference： [1]Journal of the American Chemical Society,1935,vol. 57,p. 2125

2
[ 108-16-7 ]
[ 53636-15-0 ]

Reference： [1]Patent: US2118054,1935,
[2]Journal of Medicinal Chemistry,1974,vol. 17,p. 1057 - 1060
[3]Tetrahedron Asymmetry,2003,vol. 14,p. 567 - 576

3
[ 50-00-0 ]
[ 2799-16-8 ]
[ 53636-15-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With formic acid for 24h; Heating;
	With formic acid; sodium formate
	With formic acid at 0℃; Heating / reflux;	1 In a 100 mL round-bottom flask equipped with a magnetic stirring bar, and a refrigerant, (R)-(-)-l-Amino-2-propanol (3 mL, 37 mmol) was introduced under N2 atmosphere, and cooled to 0 0C in ice bath. Formic acid (7 mL, 175 mmol) was added slowly and dropwise, followed with formaldehyde (5 mL, 67 mmol). The reaction mixture was heated at reflux for overnight, allowed to cool down at room temperature, and 6N HCI(aq) (25 mL) was added. The acidic mixture was washed with CH2CI2 (3 x 20 mL), basified to pH 13 with a slow adjunction of 50% NaOH(aq) (40 mL), and extracted with CH2CI2 (3 x 20 mL). The organic layer was dried over CaO, filtered, and allowed to warm up at 50 °C to evaporate the solvent at atmospheric pressure without a refrigerant. Crude yellowish oil 2a was obtained, and used in the next reaction without further purification.

Reference： [1]Micheli, C. De; Amici, M. De; Pratesi, P.; Grana, E.; Barbone, M. G. Santagostino [Farmaco, Edizione Scientifica, 1983, vol. 38, # 7, p. 514 - 520]
[2]Sullivan,H.R. et al. [Journal of Organic Chemistry, 1963, vol. 28, p. 2381 - 2385]
[3]Current Patent Assignee: DIAMEDICA; GENESYS VENTURE - WO2007/82381, 2007, A1 Location in patent: Page/Page column 22

4
[ 53636-15-0 ]
(S)-2-acetoxypropionic acid [ No CAS ]
L-O-Acetyllactoyl-D-β-methylnorcholin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	(i) SOCl₂, (ii) /BRN= 1719168/; Multistep reaction;

Reference： [1]Chan; Robinson [Journal of Medicinal Chemistry, 1974, vol. 17, # 10, p. 1057 - 1060]

5
[ 53636-15-0 ]
[ 18668-00-3 ]
D-O-Acetyllactoyl-D-β-methylnorcholin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	(i) SOCl₂, (ii) /BRN= 1719168/; Multistep reaction;

Reference： [1]Chan; Robinson [Journal of Medicinal Chemistry, 1974, vol. 17, # 10, p. 1057 - 1060]

6
[ 53636-15-0 ]
[ 108-24-7 ]
[ 74-88-4 ]
[ 25126-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	(i) /BRN= 385737/, iPrOH, (ii) /BRN= 969135/; Multistep reaction;

Reference： [1]Cocolas; Robinson; Dewey [Journal of medicinal chemistry, 1970, vol. 13, # 2, p. 299 - 301]

7
[ 124-40-3 ]
[ 38145-93-6 ]
[ 53636-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Inch,T.D.; Lewis,G.J. [Carbohydrate Research, 1971, vol. 16, p. 455 - 458]

8
[ 1189-71-5 ]
[ 53636-15-0 ]
C₆H₁₃ClN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane for 5h; Ambient temperature;

Reference： [1]Micheli, C. De; Amici, M. De; Pratesi, P.; Grana, E.; Barbone, M. G. Santagostino [Farmaco, Edizione Scientifica, 1983, vol. 38, # 7, p. 514 - 520]

9
[ 1189-71-5 ]
[ 53636-15-0 ]
C₆H₁₃ClN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane for 5h; Ambient temperature;

Reference： [1]Micheli, C. De; Amici, M. De; Pratesi, P.; Grana, E.; Barbone, M. G. Santagostino [Farmaco, Edizione Scientifica, 1983, vol. 38, # 7, p. 514 - 520]

10
[ 15364-56-4 ]
[ 53636-17-2 ]
[ 53636-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In methanol for 12h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With dimethylsulfide borane complex In tetrahydrofuran at 25℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With trans-RuCl₂[(R)-xylbinap][(R)-daipen]; potassium <i>tert</i>-butylate; hydrogen In isopropyl alcohol; <i>tert</i>-butyl alcohol at 25℃; for 4h; Title compound not separated from byproducts.;

Reference： [1]Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo N.; Kumobayashi, H.; et al. [Journal of the American Chemical Society, 1988, vol. 110, # 2, p. 629 - 631]
[2]Quallich, George J.; Woodall, Teresa M. [Tetrahedron Letters, 1993, vol. 34, # 26, p. 4145 - 4148]
[3]Ohkuma, Takeshi; Ishii, Dai; Takeno, Hiroshi; Noyori, Ryoji [Journal of the American Chemical Society, 2000, vol. 122, # 27, p. 6510 - 6511]

11
[ 108-16-7 ]
[ 108-05-4 ]
[ 53636-17-2 ]
[ 53636-15-0 ]
(-)-1-dimethylamino-2-propyl acetate [ No CAS ]
(S)-1-dimethylamino-2-propyl acetate [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2003,vol. 14,p. 567 - 576

12
[ 53636-15-0 ]
(S)-(+)-1-dimethylamino-2-chloropropane hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With thionyl chloride In chloroform	S-(+)-1-dimethylamino-2-chloropropane Hydrochloride, 7 S-(+)-1-dimethylamino-2-chloropropane Hydrochloride, 7 A solution of thionyl chloride (37 ml, 0.48 mol) in chloroform (20 ml) was added slowly, with stirring, to a cooled (ice/water) solution of R-(-)-1-dimethylamino-2-propanol (31.8 g, 0.32 mol) in chloroform (85 ml). When the addition was complete a precipitate formed. The mixture was allowed to warm to room temperature over 30 minutes and then heated to reflux for a further 30 minutes. The precipitate redissolved on heating but then the product crystallized out from the boiling solvent as it formed. More chloroform (20 ml) was needed to maintain the stirring. The cooled mixture was diluted with ether and filtered. The crude product (45.2 g, 89%) was recrystallized from 2-propanol and decolourising charcoal was used. The product (33.1 g, 65%) was obtained in 3 crops and the first crop (24.5 g) was kept separate; [α]D +59.1° (c 2.075, H2 O).
31%	With thionyl chloride In chloroform for 0.5h; Heating;

Reference： [1]Current Patent Assignee: SCHEINMANN - US6143933, 2000, A
[2]Hull, Jonathan D.; Scheinmann, Feodor; Turner, Nicholas J. [Tetrahedron Asymmetry, 2003, vol. 14, # 5, p. 567 - 576]

13
[ 200334-62-9 ]
[ 53636-15-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium methylate In methanol

Reference： [1]Hull, Jonathan D.; Scheinmann, Feodor; Turner, Nicholas J. [Tetrahedron Asymmetry, 2003, vol. 14, # 5, p. 567 - 576]

14
[ 15364-56-4 ]
C₁₀H₂₄N₂O₂ [ No CAS ]
[ 53636-17-2 ]
[ 53636-15-0 ]

Yield	Reaction Conditions	Operation in experiment
8%	With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide; isopropyl alcohol Electrochemical reaction;

Reference： [1]Yadav, Ashok K.; Manju, Meera [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 12, p. 2770 - 2772]

15
[ 53636-15-0 ]
[ 86919-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hexane / 5 h / Ambient temperature 2: 20percent K₂CO₃

Reference： [1]Micheli, C. De; Amici, M. De; Pratesi, P.; Grana, E.; Barbone, M. G. Santagostino [Farmaco, Edizione Scientifica, 1983, vol. 38, # 7, p. 514 - 520]

16
[ 53636-15-0 ]
[ 86975-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hexane / 5 h / Ambient temperature 2: 20percent K₂CO₃

Reference： [1]Micheli, C. De; Amici, M. De; Pratesi, P.; Grana, E.; Barbone, M. G. Santagostino [Farmaco, Edizione Scientifica, 1983, vol. 38, # 7, p. 514 - 520]

17
[ 53636-15-0 ]
[ 98557-13-2 ]
2,(S)-α-dichlorphenyl-acetic acid (R)-1-(dimethylamino)-2-propyl ester hydrochloride [ No CAS ]
2,(R)-α-dichlorphenyl-acetic acid (R)-1-(dimethylamino)-2-propyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In tetrahydrofuran at 20 - 55℃; for 2.33333h;

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - EP1589019, 2005, A1 Location in patent: Page/Page column 40

18
(R)-1-(dimethylamino)-2-propanoldibenzoyl-L-tartrate hydrochloride [ No CAS ]
[ 53636-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; water Resolution of racemate;

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - EP1589019, 2005, A1 Location in patent: Page/Page column 40

19
[ 1189-71-5 ]
[ 53636-15-0 ]
[ 86919-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane at 0 - 20℃;	1 In a 250 mL round-bottom flask equipped with a magnetic stirring bar, (R)-(-)-l-Diamino-2-propanol (2a) (5 mL, 40 mmol), and dry hexanes (80 mL) were added under N2 atmosphere. The mixture was cooled to 0 °C in ice bath. Through a dropping funnel, a solution of chlorosulfonyl isocyanate (14 mL, 159 mmol) in dry hexanes (60 mL) was added slowly and dropwise under strong stirring. A colourless precipitate rapidly formed. The mixture was allowed to warm up to room temperature. The stirring was maintained for overnight. The reaction mixture was cooled to 0 0C, and under strong stirring water was cautiously added dropwise until all the precipitate was dissolved. The aqueous layer was washed with CH2CI2 (3 x 20 mL), basified to pH 13 with a cautious slow adjunction of 50% NaOH (aq) (50 mL), and extracted with CH2CI2 (3 x 20 mL). The organic layer was dried over MgSO4, filtered, and evaporated to dryness under reduced pressure to obtain colourless oil 3a that crystallized at room temperature.

Reference： [1]Current Patent Assignee: DIAMEDICA; GENESYS VENTURE - WO2007/82381, 2007, A1 Location in patent: Page/Page column 23

20
[ 53636-15-0 ]
[ 1445-79-0 ]
dimethylgallium(+)(-)dimethylamino-2-propoxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In pentane byproducts: CH4; Ar-atmosphere; dropwise addn. of equimolar amt. of amine to Ga-compd. at-20°C, warming to room temp.; solvent removal (vac.), sublimation (69°C, 3 Torr); elem. anal.;

Reference： [1]Thiele, Karl-Heinz; Hecht, Elmar; Gelbrich, Thomas; Duemichen, Ulf [Journal of Organometallic Chemistry, 1997, vol. 540, # 1-2, p. 89 - 94]

21
[ 53636-15-0 ]
[ 75-24-1 ]
dimethylaluminum(+)(-)dimethylamino-2-propoxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In pentane byproducts: CH4; Ar-atmosphere; dropwise addn. of equimolar amt. of amine to Al-compd. at-15°C, warming to room temp.; solvent removal (vac.), sublimation (66°C, 3 Torr); elem. anal.;

Reference： [1]Thiele, Karl-Heinz; Hecht, Elmar; Gelbrich, Thomas; Duemichen, Ulf [Journal of Organometallic Chemistry, 1997, vol. 540, # 1-2, p. 89 - 94]

22
(R)-1-(dimethylamino)-2-propanyl butyrate [ No CAS ]
[ 53636-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium hydroxide In methanol optical yield given as %ee;

Reference： [1]Location in patent: experimental part Brossat, Maude; Moody, Thomas S.; Taylor, Stephen J.C.; Wiffen, Jonathan W. [Tetrahedron Asymmetry, 2009, vol. 20, # 18, p. 2112 - 2116]

23
[ 53636-15-0 ]
[ 93-97-0 ]
(R)-1-(dimethylamino)-2-propanyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (R)-1-(dimethylamino)-2-propanol; benzoic acid anhydride at 70℃; for 0.166667h; Stage #2: With hydrogenchloride; water In tert-butyl methyl ether Stage #3: With water; sodium hydroxide optical yield given as %ee;

Reference： [1]Location in patent: experimental part Brossat, Maude; Moody, Thomas S.; Taylor, Stephen J.C.; Wiffen, Jonathan W. [Tetrahedron Asymmetry, 2009, vol. 20, # 18, p. 2112 - 2116]

24
[ 98956-88-8 ]
[ 53636-17-2 ]
[ 53636-15-0 ]
(R)-1-(dimethylamino)-2-propanyl butyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Bacillus licheniformis subtilisin; water at 20℃; for 16h; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;

Reference： [1]Location in patent: experimental part Brossat, Maude; Moody, Thomas S.; Taylor, Stephen J.C.; Wiffen, Jonathan W. [Tetrahedron Asymmetry, 2009, vol. 20, # 18, p. 2112 - 2116]

25
[ 53636-15-0 ]
[ 34617-65-7 ]
[ 1184843-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 100 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 0.75 h / 130 °C / Inert atmosphere; Microwave irradiation 2.2: acidic ion exchange column / Inert atmosphere

Reference： [1]Reader, John C.; Matthews, Thomas P.; Klair, Suki; Cheung, Kwai-Ming J.; Scanlon, Jane; Proisy, Nicolas; Addison, Glynn; Ellard, John; Piton, Nelly; Taylor, Suzanne; Cherry, Michael; Fisher, Martin; Boxall, Kathy; Burns, Samantha; Walton, Michael I.; Westwood, Isaac M.; Hayes, Angela; Eve, Paul; Valenti, Melanie; De Haven Brandon, Alexis; Box, Gary; Van Montfort, Rob L. M.; Williams, David H.; Aherne, G. Wynne; Raynaud, Florence I.; Eccles, Suzanne A.; Garrett, Michelle D.; Collins, Ian [Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8328 - 8342]

26
[ 53636-15-0 ]
[ 34617-65-7 ]
[ 1184843-17-1 ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: (R)-1-(dimethylamino)-2-propanol With sodium hydride In 1,4-dioxane; mineral oil for 0.5h; Inert atmosphere; Stage #2: 5-amino-3-chloro-pyrazine-2-carbonitrile In 1,4-dioxane; mineral oil at 90℃; for 14h; Inert atmosphere;
39%	Stage #1: (R)-1-(dimethylamino)-2-propanol With sodium hydride In 1,4-dioxane; mineral oil for 0.5h; Inert atmosphere; Stage #2: 5-amino-3-chloro-pyrazine-2-carbonitrile In 1,4-dioxane; mineral oil at 90℃; for 14h; Inert atmosphere;
39%	Stage #1: (R)-1-(dimethylamino)-2-propanol With sodium hydride In 1,4-dioxane; mineral oil for 0.5h; Stage #2: 5-amino-3-chloro-pyrazine-2-carbonitrile In 1,4-dioxane; mineral oil at 90℃; for 14h;	(R)-5-Amino-3-((1-(dimethylamino)propan-2-yl)oxy)pyrazine-2-carbonitrile (f?)-1-(Dimethylamino)propan-2-ol (0.667 g, 6.47 mmol) was added dropwise to a suspension of NaH (60% in oil; 0.388 g, 9.71 mmol) in dioxane (16.2 mL) and stirred for 30 minutes. 5-Amino-3-chloropyrazine-2-carbonitrile (Intermediate I-2) (1.00 g,6.47 mmol) was added in one portion and the mixture was heated at 90 °C for 14 hours. After cooling, water (200 mL) was added and the solution was extracted with Et20 (4 x 100 mL), dried over MgS04, and the volatiles removed under vacuum. Gradient column chromatography eluting with MeOH: 1 % NH3 in CH2CI2, gave (f?)-5-amino-3-((1 - (dimethylamino)propan-2-yl)oxy)pyrazine-2-carbonitrile (0.558 g, 2.52 mmol, 39% yield) as a yellow solid.1H NMR (500 MHz, CDCI3) ? 7.54 (s, 1 H), 5.42-5.35 (m, 1 H), 5.31 (brs, 2H), 2.76 (dd, J = 7.5, 13.5, 1 H), 2.52 (dd, J = 4.0, 13.5, 1 H), 2.37 (s, 6H), 1.35 (d, J = 6.5, 3H); LC-MS (LCT, 3.5 minutes) Rt = 0.80 minutes; m/z (ESI) 222 (M+H).

With sodium hydride In 1,4-dioxane; mineral oil at 100℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Reader, John C.; Matthews, Thomas P.; Klair, Suki; Cheung, Kwai-Ming J.; Scanlon, Jane; Proisy, Nicolas; Addison, Glynn; Ellard, John; Piton, Nelly; Taylor, Suzanne; Cherry, Michael; Fisher, Martin; Boxall, Kathy; Burns, Samantha; Walton, Michael I.; Westwood, Isaac M.; Hayes, Angela; Eve, Paul; Valenti, Melanie; De Haven Brandon, Alexis; Box, Gary; Van Montfort, Rob L. M.; Williams, David H.; Aherne, G. Wynne; Raynaud, Florence I.; Eccles, Suzanne A.; Garrett, Michelle D.; Collins, Ian [Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8328 - 8342]
[2]Lainchbury, Michael; Matthews, Thomas P.; McHardy, Tatiana; Boxall, Kathy J.; Walton, Michael I.; Eve, Paul D.; Hayes, Angela; Valenti, Melanie R.; De Haven Brandon, Alexis K.; Box, Gary; Aherne, G. Wynne; Reader, John C.; Raynaud, Florence I.; Eccles, Suzanne A.; Garrett, Michelle D.; Collins, Ian [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10229 - 10240]
[3]Current Patent Assignee: CANCER RESEARCH UK - WO2013/68755, 2013, A1 Location in patent: Page/Page column 68
[4]Location in patent: scheme or table Reader, John C.; Matthews, Thomas P.; Klair, Suki; Cheung, Kwai-Ming J.; Scanlon, Jane; Proisy, Nicolas; Addison, Glynn; Ellard, John; Piton, Nelly; Taylor, Suzanne; Cherry, Michael; Fisher, Martin; Boxall, Kathy; Burns, Samantha; Walton, Michael I.; Westwood, Isaac M.; Hayes, Angela; Eve, Paul; Valenti, Melanie; De Haven Brandon, Alexis; Box, Gary; Van Montfort, Rob L. M.; Williams, David H.; Aherne, G. Wynne; Raynaud, Florence I.; Eccles, Suzanne A.; Garrett, Michelle D.; Collins, Ian [Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8328 - 8342]

27
[ 124-40-3 ]
[ 15448-47-2 ]
[ 53636-15-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	In water at 20℃; for 2h; Inert atmosphere; Cooling with ice;
40%	In water at 20℃; for 2h; Cooling with ice;	(R)-1-(Dimethylamino)propan-2-ol Dimethylamine 40% in water (1 1 .39 mL, 90 mmol) was slowly added to (f?)-propylene oxide (5.25 mL, 74.9 mmol) which had been cooled in an ice bath. This solution was stirred at room temperature for 2 hours before being extracted with CH2CI2 (4 x 5 mL). The combined organic layers were dried over Na2S04 and pure (f?)-1 - (dimethylamino)propan-2-ol (5.12 g, 49.6 mmol, 40% yield) was isolated as a clear oil by distillation under reduced pressure (50 mbar).1H NMR (CDCIs, 500 MHz) ? 3.82-3.76 (m, 1 H), 3.40 (brs, 1 H), 2.27 (s, 6H), 2.25-2.21 (m, 1 H), 2.16-2.12 (m, 1 H), 1.12 (d, J = 6.0, 3H).

28
[ 53636-15-0 ]
[ 1404095-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Lainchbury, Michael; Matthews, Thomas P.; McHardy, Tatiana; Boxall, Kathy J.; Walton, Michael I.; Eve, Paul D.; Hayes, Angela; Valenti, Melanie R.; De Haven Brandon, Alexis K.; Box, Gary; Aherne, G. Wynne; Reader, John C.; Raynaud, Florence I.; Eccles, Suzanne A.; Garrett, Michelle D.; Collins, Ian [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10229 - 10240]

29
[ 53636-15-0 ]
[ 1404095-24-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

30
[ 53636-15-0 ]
[ 1404095-25-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

31
[ 53636-15-0 ]
[ 1404095-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

32
[ 53636-15-0 ]
[ 1404095-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

33
[ 53636-15-0 ]
[ 1404095-28-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / toluene / 0.75 h / 130 °C / Inert atmosphere; Microwave irradiation

34
[ 53636-15-0 ]
[ 1404095-34-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1,4-dioxane / 17 h / 100 °C / Inert atmosphere

35
[ 53636-15-0 ]
[ 1404095-37-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

36
[ 53636-15-0 ]
[ 1404095-11-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / toluene / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

37
[ 53636-15-0 ]
[ 1404095-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

38
[ 53636-15-0 ]
[ 1404095-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / 1,4-dioxane; mineral oil / 0.5 h / Inert atmosphere 1.2: 14 h / 90 °C / Inert atmosphere 2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

39
[ 53636-15-0 ]
tert-butyl 4-(7-benzyl-2-chloro-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl)-2-(cyanomethyl)piperazine-1-carboxylate [ No CAS ]
tert-butyl 4-[7-benzyl-2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]-2-(cyanomethyl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
300 mg	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 90℃; for 5h;	150.A Step A: tert-Butyl 4-[7-benzyl-2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]-2-(cyanomethyl)piperazine-1-carboxylate: To a mixture of tert-butyl 4-(7-benzyl-2-chloro-6,8-dihydro-5H- pyrido[3,4-
300 mg	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 90℃; for 5h; Inert atmosphere;	150.A Example 150 2-(1-acryloyl-4-(2-(((R)-1-(dimethylamino)propan-2-yl)oxy)-7-(3-hydroxynap- hthalen-1-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazin-2-yl- )acetonitrile Step A: tert-Butyl 4-[7-benzyl-2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-6,8-dihydro-5H-pyr- ido[3,4-d]pyrimidin-4-yl]-2-(cyanomethyl)piperazine-1-carboxylate To a mixture of tert-butyl 4-(7-benzyl-2-chloro-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl)-2-(cyano- methyl)piperazine-1-carboxylate (500 mg, 1.04 mmol), (2R)-1-(dimethylamino)propan-2-ol (214 mg, 2.07 mmol and sodium tert-butoxide (298 mg, 3.11 mmol) in toluene (20 mL) was added BINAP (129 mg, 207 umol) and Pd 2(dba) 3 (94.8 mg, 104 umol) and the mixture was sparged with nitrogen followed by stirring at 90° C. for 5 hr. The mixture was diluted with ethyl acetate (100 mL) and water (100 mL) and the organic layer was separated and dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by reversed phase flash chromatogaphy [water (0.1% Formic Acid water)/acetonitrile]. The desired fractions were collected and neutralized with saturated aqueous sodium carbonate solution (5 mL) and extracted with 10% MeOH/DCM (2 50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated under vacuum to give tert-Butyl 4-[7-benzyl-2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-6,8-dihydro-5H-pyr- ido[3,4-d]pyrimidin-4-yl]-2-(cyanomethyl)piperazine-1-carboxylate (300 mg, 480 umol) ES+APCI MS m/z 550.4 [M+H] +.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2017/201161, 2017, A1 Location in patent: Paragraph 0601
[2]Current Patent Assignee: PFIZER INC; MIRATI THERAPEUTICS, INC. - US2019/144444, 2019, A1 Location in patent: Paragraph 0989-0990

40
[ 53636-15-0 ]
4-(7-(5-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-4-yl)-2-(methyl sulfoxide)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazin-1-carboxylic acid benzyl ester [ No CAS ]
benzyl 4-[2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-7-[5-methyl-1-(2-trimethylsilylethoxymethyl)indazol-4-yl]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
280 mg	With sodium t-butanolate In toluene at 15℃; for 0.5h;	162.A Step A: benzyl 4-[2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-7-[5-methyl-1-(2-trimethylsilylethoxymethyl)indazol-4-yl]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]piperazine-1-carboxylate: A mixture of (2R)-l-(dimethylamino)propan-2-ol (183 mg, 1.78 mmol) (8.00 mL), benzyl 4-[2-methylsulfinyl-7-[5-methyl-l-(2- trimethylsilylethoxymethyl)indazol-4-yl]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4- yl]piperazine-l-carboxylate (400 mg, 592 umol) and NaOtBu (114 mg, 1.18 mmol) in toluene were stirred at 15 °C for 0.5 hour. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography over AI2O3 (Petroleum Ether/EthylAcetate 10/1 to 0/1) to give benzyl 4-[2-[(lR)-2-(dimethylamino)-l- methyl-ethoxy]-7-[5-methyl-l-(2-trimethylsilylethoxymethyl)indazol-4-yl]-6,8-dihydro-5H- pyrido[3,4-d]pyrimidin-4-yl]piperazine-l-carboxylate (280 mg, 352 umol). 1H MR (400 MHz, chloroform-d) δ = 8.08 (s, 1H), 7.46 - 7.39 (m, 5H), 7.38 - 7.33 (m, 2H), 5.76 (s, 2H), 5.43 - 5.33 (m, 1H), 5.24 (s, 2H), 4.35 (s, 2H), 3.72 - 3.67 (m, 4H), 3.64 - 3.56 (m, 4H), 3.55 - 3.47 (m, 4H), 2.87 - 2.80 (m, 2H), 2.74 (dd, J=6.8, 12.8 Hz, 1H), 2.49 (s, 3H), 2.47 - 2.40 (m, 1H), 2.36 (s, 6H), 1.42 (d, J=6.4 Hz, 3H), 0.98 - 0.92 (m, 2H), 0.00 (s, 9H).
280 mg	With sodium t-butanolate In toluene at 15℃; for 0.5h;	162.A Example 162 1-[4-[2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-7-(5-methyl-1H-indazol-4-- yl)-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]piperazin-1-yl]prop-2-en-1-- one Step A: benzyl 4-[2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-7-[5-methyl-1-(2-trimethyls- ilylethoxymethyl)indazol-4-yl]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]- piperazine-1-carboxylate A mixture of (2R)-1-(dimethylamino)propan-2-ol (183 mg, 1.78 mmol) (8.00 mL), benzyl 4-[2-methylsulfinyl-7-[5-methyl-1-(2-trimethylsilylethoxymethyl)indazol-4- -yl]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]piperazine-1-carboxylate (400 mg, 592 umol) and NaOtBu (114 mg, 1.18 mmol) in toluene were stirred at 15° C. for 0.5 hour. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography over Al 2O 3 (Petroleum Ether/EthylAcetate 10/1 to 0/1) to give benzyl 4-[2-[(1R)-2-(dimethylamino)-1-methyl-ethoxy]-7-[5-methyl-1-(2-trimethyls- ilylethoxymethyl)indazol-4-yl]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]- piperazine-1-carboxylate (280 mg, 352 umol). 1H NMR (400 MHz, chloroform-d) δ=8.08 (s, 1H), 7.46-7.39 (m, 5H), 7.38-7.33 (m, 2H), 5.76 (s, 2H), 5.43-5.33 (m, 1H), 5.24 (s, 2H), 4.35 (s, 2H), 3.72-3.67 (m, 4H), 3.64-3.56 (m, 4H), 3.55-3.47 (m, 4H), 2.87-2.80 (m, 2H), 2.74 (dd, J=6.8, 12.8 Hz, 1H), 2.49 (s, 3H), 2.47-2.40 (m, 1H), 2.36 (s, 6H), 1.42 (d, J=6.4 Hz, 3H), 0.98-0.92 (m, 2H), 0.00 (s, 9H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2017/201161, 2017, A1 Location in patent: Paragraph 0637
[2]Current Patent Assignee: PFIZER INC; MIRATI THERAPEUTICS, INC. - US2019/144444, 2019, A1 Location in patent: Paragraph 1037-1038

41
[ 53636-15-0 ]
[ 74-88-4 ]
[ 54770-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 20℃;

Reference： [1]Zuo, Wei; Huang, Zhe; Zhao, Yanxia; Xu, Wenhua; Liu, Zhihua; Yang, Xiao-Juan; Jia, Chuandong; Wu, Biao [Chemical Communications, 2018, vol. 54, # 53, p. 7378 - 7381]

42
[ 53636-15-0 ]
C₆H₁₆NO⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 20 °C 2: potassium hexafluorophosphate / water / 1 h / 20 °C

Reference： [1]Zuo, Wei; Huang, Zhe; Zhao, Yanxia; Xu, Wenhua; Liu, Zhihua; Yang, Xiao-Juan; Jia, Chuandong; Wu, Biao [Chemical Communications, 2018, vol. 54, # 53, p. 7378 - 7381]

43
[ 53636-15-0 ]
C₆H₁₆NO⁽¹⁺⁾*3C₄₁H₃₄N₁₀O₈*2O₄P^(3-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 20 °C 2: potassium hexafluorophosphate / water / 1 h / 20 °C 3: acetonitrile / 20 °C

Reference： [1]Zuo, Wei; Huang, Zhe; Zhao, Yanxia; Xu, Wenhua; Liu, Zhihua; Yang, Xiao-Juan; Jia, Chuandong; Wu, Biao [Chemical Communications, 2018, vol. 54, # 53, p. 7378 - 7381]

44
[ 573675-25-9 ]
[ 53636-15-0 ]
(R)-N<SUP>4</SUP>-methyl-5-(1-methyl-1H-pyrazol-4-yl)-N<SUP>2</SUP>-(2-cyano-3-(1-(dimethylamino)prop-2-yloxy)pyridin-5-yl)-2,4-diaminopyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 3 h / 0 - 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 101 °C / Inert atmosphere

Reference： [1]Tong, Lexian; Song, Pinrao; Jiang, Kailong; Xu, Lei; Jin, Tingting; Wang, Peipei; Hu, Xiaobei; Fang, Sui; Gao, Anhui; Zhou, Yubo; Liu, Tao; Li, Jia; Hu, Yongzhou [European Journal of Medicinal Chemistry, 2019, vol. 173, p. 44 - 62]

45
[ 573675-25-9 ]
[ 53636-15-0 ]
(R)-5-bromo-3-((1-(dimethylamino)propan-2-yl)oxy)picolinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: A mixture of sodium hydrogen (7.5 mmol), appropriate alcohol(5.0 mmol) in dry THF (100 mL) was cooled at 0 C, then themixture was stirred at room temperature for 30 min. Adding thereaction liquid to the mixture of <strong>[573675-25-9]5-bromo-3-nitropicolinonitrile</strong>(5.0 mmol) in 50 THF (50 mL) dropwise at 0 C then the mixturewas stirred at rt for 3 h. The reaction solution was treated withsaturated NH4Cl and was extracted with EtOAc. The organic layerwas collected, washed with brine, and dried over MgSO4, concentrated.The residue obtained was purified by column chromatography(eluent gradient 10-20% petroleum ether in EtOAc), gave42a-k.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 173,p. 44 - 62

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H200	Unstable explosive
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 53636-15-0 ] Synthesis Path-Downstream 1~45

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