[ CAS No. 10325-70-9 ] {[proInfo.proName]}

Name: 10325-70-9|5-Acetylpyrimidine|95%
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Quality Control of [ 10325-70-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 10325-70-9 ]

CAS No. :	10325-70-9	MDL No. :	MFCD09038477
Formula :	C₆H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	COTYNDRSENVEFI-UHFFFAOYSA-N
M.W :	122.12	Pubchem ID :	572308
Synonyms :

Calculated chemistry of [ 10325-70-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.23
TPSA :	42.85 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.11
Log Po/w (XLOGP3) :	-0.11
Log Po/w (WLOGP) :	0.68
Log Po/w (MLOGP) :	-0.7
Log Po/w (SILICOS-IT) :	1.19
Consensus Log Po/w :	0.43

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.96
Solubility :	13.5 mg/ml ; 0.111 mol/l
Class :	Very soluble
Log S (Ali) :	-0.34
Solubility :	56.2 mg/ml ; 0.46 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.94
Solubility :	1.4 mg/ml ; 0.0115 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.04

Safety of [ 10325-70-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 10325-70-9 ]

* 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 [ 10325-70-9 ]
Downstream synthetic route of [ 10325-70-9 ]

[ 10325-70-9 ] Synthesis Path-Upstream 1~7

1
[ 4595-59-9 ]
[ 78191-00-1 ]
[ 10325-70-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Stage #2: at -78 - 0℃;	Step A: 5-Acetylpyrimidine 5-Bromopyrimidine (3.18 g, 20 mmol) was dissolved in 50 mL of tetrahydrofuran, While cooled to -78 °C, 15 mL of 1.6 M n-butolithium in hexane solution was added dropwise with stirring, After the solution was stirred for 30 minutes, a solution of N-methoxyl-N-methylacetamide (2.58 g, 25 mmol) in tetrahydrofuran solution (10 mL) was added slowly. The mixture was stirred at -78 °C for 1 hour and then allowed to be warmed slowly. When the temperature of the mixture was at 0 °C, aqueous ammonium chloride solution was added. The solution obtained was extracted with ethyl acetate for 3 times, The pooled extracts were washed with brine, dried over magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography using 5percent methanol / methylene chloride as eluent to obtain 1 g of the title compound (45percent yield). MS(M+1)=123.05.
175 mg	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; Stage #2: at -78℃; for 1 h;	The5-bromo-pyrimidine (9.4 mmol) is dissolved in tetrahydrofuran steams again 30ml in. At -78 ° C lower, will n-BuLi (11.3 mmol) in drops to the reactionsystem, and stirring 30 minutes. N-methoxy-N-methyl acetamide (11.8 mmol) oftetrahydrofuran solution (15 ml) at -78 ° C in the system dropping, andstirring 1 hour. Under room temperature, add saturated ammonium chlorideaqueous solution, ethyl acetate extraction 3 times. Concentrated extract,column chromatography (ethyl acetate: petroleum ether = 1 the [...] 10)separated to obtain title compound 175 mg per litre. ¹ H-NMR (CDCl ₃)δ 9.37 (1H, s), 9.24 (2H, s), 2.66 (3H, s).

Reference： [1] Patent: EP2385035, 2011, A1, . Location in patent: Page/Page column 18-19
[2] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0178-0180

2
[ 79691-74-0 ]
[ 10325-70-9 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1981, vol. 17, # 7, p. 710 - 714[2] Khimiya Geterotsiklicheskikh Soedinenii, 1981, # 7, p. 958 - 962
[3] Archiv der Pharmazie, 2001, vol. 334, # 3, p. 79 - 85

3
[ 60025-06-1 ]
[ 10325-70-9 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1981, vol. 17, # 7, p. 710 - 714[2] Khimiya Geterotsiklicheskikh Soedinenii, 1981, # 7, p. 958 - 962

4
[ 60025-05-0 ]
[ 10325-70-9 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1981, vol. 17, # 7, p. 710 - 714[2] Khimiya Geterotsiklicheskikh Soedinenii, 1981, # 7, p. 958 - 962

5
[ 10070-92-5 ]
[ 10325-70-9 ]

Reference： [1] Archiv der Pharmazie, 2001, vol. 334, # 3, p. 79 - 85

6
[ 693-98-1 ]
[ 10325-70-9 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 6 - 10[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 1, p. 9 - 14

7
[ 789-24-2 ]
[ 27839-58-3 ]
[ 10325-70-9 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 6 - 10[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 1, p. 9 - 14

[ 10325-70-9 ] Synthesis Path-Downstream 1~48

1
[ 79691-74-0 ]
[ 10325-70-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1981,vol. 17,p. 710 - 714
Khimiya Geterotsiklicheskikh Soedinenii,1981,p. 958 - 962
[2]Archiv der Pharmazie,2001,vol. 334,p. 79 - 85

2
[ 60025-06-1 ]
[ 10325-70-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1981,vol. 17,p. 710 - 714
Khimiya Geterotsiklicheskikh Soedinenii,1981,p. 958 - 962

3
[ 693-98-1 ]
C₆H₅N₂O^(1-)*K⁽¹⁺⁾ [ No CAS ]
potassium 2-methylimidazolate [ No CAS ]
[ 10325-70-9 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 6 - 10
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 9 - 14

4
[ 789-24-2 ]
C₆H₅N₂O^(1-)*K⁽¹⁺⁾ [ No CAS ]
[ 27839-58-3 ]
[ 10325-70-9 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 6 - 10
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 9 - 14

5
[ 27839-58-3 ]
[ 10325-70-9 ]
[ 789-24-2 ]
C₆H₅N₂O^(1-)*K⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 6 - 10
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 9 - 14

6
potassium 2-methylimidazolate [ No CAS ]
[ 10325-70-9 ]
[ 693-98-1 ]
C₆H₅N₂O^(1-)*K⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 6 - 10
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 9 - 14

8
[ 593-56-6 ]
[ 10325-70-9 ]
(Z)-1-(pyrimidin-5-yl)-ethanone O-methyloxime [ No CAS ]
[ 349493-42-1 ]

Reference： [1]Archiv der Pharmazie,2001,vol. 334,p. 79 - 85

9
[ 10325-70-9 ]
3-methyl-isoxazolo[5,4-d]pyrimidine [ No CAS ]
[ 349493-40-9 ]

Reference： [1]Archiv der Pharmazie,2001,vol. 334,p. 79 - 85

10
[ 10070-92-5 ]
[ 10325-70-9 ]

Reference： [1]Archiv der Pharmazie,2001,vol. 334,p. 79 - 85

11
[ 10325-70-9 ]
1-(3-methyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-ethanone <i>O</i>-methyl-oxime [ No CAS ]

Reference： [1]Archiv der Pharmazie,2001,vol. 334,p. 79 - 85

12
[ 10325-70-9 ]
5-{1-[(E)-Methoxyimino]-ethyl}-1-methyl-pyrimidin-1-ium; iodide [ No CAS ]

Reference： [1]Archiv der Pharmazie,2001,vol. 334,p. 79 - 85

13
[ 60025-05-0 ]
[ 10325-70-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1981,vol. 17,p. 710 - 714
Khimiya Geterotsiklicheskikh Soedinenii,1981,p. 958 - 962

14
[ 4637-24-5 ]
[ 10325-70-9 ]
[ 641615-34-1 ]

Yield	Reaction Conditions	Operation in experiment
	for 15h;Heating / reflux;	3-(dimethylamino)-1-(5-pyrimidinyl)-2-propen-1-one This compound was prepared by version of the method described in the document (Japanese Unexamined Patent Publication (Kokai) No. 6-87834). 6.01 g of N,N-dimethylformamide dimethylacetal was added to 1.54 g of <strong>[10325-70-9]5-acetylpyrimidine</strong> (Khim. Geterotsikl. Soedim., 1981, (7), 958-962) and the mixture was heated at reflux for 15 hours. After the reaction solution was air-cooled, a small amount of diisopropyl ether was added and the deposited crystal was collected by filtration to obtain 1.52 g of the objective compound as a reddish brown crystal. Melting point: 133-135C 1H-NMR(CDCl3)delta: 2.98(3H, s), 3.22(3H, s), 5.62(1H, d), 7.89(1H, d), 9.17(2H, s), 9.27(1H, s)
	for 15h;Heating / reflux;	Step 1 3-(dimethylamino)-1-(5-pyrimidinyl)-2-propen-1-one 6.01 g of N,N-dimethylformamide dimethylacetal was added to 1.54 g of <strong>[10325-70-9]5-acetylpyrimidine</strong> ( ) and the mixture was heated at reflux for 15 hours. After the reaction solution was air-cooled, a small amount of diisopropyl ether was added and the deposited crystal was collected by filtration to obtain 1.52 g of the objective compound as reddish brown crystals. Melting point: 133-135C

Reference： [1]Patent: EP1533304,2005,A1 .Location in patent: Page/Page column 15
[2]Patent: EP1702917,2006,A1 .Location in patent: Page/Page column 32

15
[ 1072-85-1 ]
[ 10325-70-9 ]
[ 1213251-48-9 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1032 - 1035

16
[ 50998-17-9 ]
[ 10325-70-9 ]
[ 1213251-59-2 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1032 - 1035

17
[ 4637-24-5 ]
[ 10325-70-9 ]
[ 1232062-67-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	In isopropyl alcohol; at 100℃; for 24h;	Step B: (2E)-3-(Dimethylamino)-1-pyrimidin-5-ylprop-2-en-1-one 5-Acetylpyrimidine (1 g, 8.2 mmol) and N,N-dimethylformamide dimethyl acetal (1.3 g, 11 mmol) were dissolved in 20 mL of isopropanol. The solution was stirred at 100 C for 24 hours, cooled to room temperature, and concentrated under reduced pressure. Ethyl ether was then added to the residue. After being cooled in an ice bath for a couple of hours, the solid was collected by filtration, rinsed with cold ethyl ether, dried in vacuum to obtain 1 g (59% yield) of the title compound. MS(M+1)=178.0.
657 mg	for 2h;Reflux;	553-1 A mixture of <strong>[10325-70-9]1-(pyrimidin-5-yl)ethanone</strong> (525 mg) and N,N-dimethylformamide dimethyl acetal (3 mL) was stirred for 2 hours under heating to reflux. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. tert-Butyl methyl ether was added to the obtained residue, and the solid matter was collected by filtration, thereby obtaining (E)-3-(dimethylamino)-1-(pyrimidin-5-yl)prop-2-en-1-one (657 mg). MS m/z (M+H): 178.

Reference： [1]Patent: EP2385035,2011,A1 .Location in patent: Page/Page column 19
[2]Patent: US2015/322063,2015,A1 .Location in patent: Paragraph 2651; 2652; 2653

18
[ 4595-59-9 ]
[ 78191-00-1 ]
[ 10325-70-9 ]

Yield	Reaction Conditions	Operation in experiment
45%		Step A: 5-Acetylpyrimidine 5-Bromopyrimidine (3.18 g, 20 mmol) was dissolved in 50 mL of tetrahydrofuran, While cooled to -78 C, 15 mL of 1.6 M n-butolithium in hexane solution was added dropwise with stirring, After the solution was stirred for 30 minutes, a solution of N-methoxyl-N-methylacetamide (2.58 g, 25 mmol) in tetrahydrofuran solution (10 mL) was added slowly. The mixture was stirred at -78 C for 1 hour and then allowed to be warmed slowly. When the temperature of the mixture was at 0 C, aqueous ammonium chloride solution was added. The solution obtained was extracted with ethyl acetate for 3 times, The pooled extracts were washed with brine, dried over magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography using 5% methanol / methylene chloride as eluent to obtain 1 g of the title compound (45% yield). MS(M+1)=123.05.
175 mg		The5-bromo-pyrimidine (9.4 mmol) is dissolved in tetrahydrofuran steams again 30ml in. At -78 C lower, will n-BuLi (11.3 mmol) in drops to the reactionsystem, and stirring 30 minutes. N-methoxy-N-methyl acetamide (11.8 mmol) oftetrahydrofuran solution (15 ml) at -78 C in the system dropping, andstirring 1 hour. Under room temperature, add saturated ammonium chlorideaqueous solution, ethyl acetate extraction 3 times. Concentrated extract,column chromatography (ethyl acetate: petroleum ether = 1 the [...] 10)separated to obtain title compound 175 mg per litre. 1 H-NMR (CDCl 3)delta 9.37 (1H, s), 9.24 (2H, s), 2.66 (3H, s).

Reference： [1]Patent: EP2385035,2011,A1 .Location in patent: Page/Page column 18-19
[2]Patent: CN103130792,2016,B .Location in patent: Paragraph 0178-0180

19
[ 10325-70-9 ]
[ 641615-36-3 ]

Reference： [1]Patent: EP2385035,2011,A1

20
[ 10325-70-9 ]
[ 641615-35-2 ]

Reference： [1]Patent: EP2385035,2011,A1

21
[ 10325-70-9 ]
[ 1232061-97-0 ]

Reference： [1]Patent: EP2385035,2011,A1

22
[ 1585971-57-8 ]
[ 10325-70-9 ]
[ 1616100-96-9 ]

Yield	Reaction Conditions	Operation in experiment
46.4%		Preparation 84 (R)-N-((5)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane- 2-sulfinamide To a solution of l-(pyrimidin-5-yl)ethanone (2.072 g, 16.97 mmol) in DMF (40 mL) was added 60 % wt aH (0.747 g, 18.66 mmol) at 0 C under nitrogen. The mixture was stirred at 0 C for 30 min. A solution of (R,£)-N-(l-(2,4-difluorophenyl)ethylidene)-2- methylpropane-2-sulfinamide from preparation 73 (2.2 g, 8.48 mmol) in DMF (4 mL) was slowly added at -10 C under nitrogen. The mixture was stirred from -10 C to -5 C over 1.5 h. The reaction was quenched with water, and extracted with 2x250 mL of ethyl acetate. The combined organic layers were removed, dried over sodium sulfate, and concentrated. The residue was purified via silica gel chromatography (gradient elution using ethyl acetate to 10% methanol in ethyl acetate) to give (R)-N-((5)-2-(2,4- difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide (1.5 g, 3.93 mmol, 46.4 % yield). MS (M+H)+ = 382.05. 1H NMR (500MHz, CHLOROFORM-d) delta 9.37 (s, 1H), 9.18 (s, 2H), 7.61 (td, J=9.3, 6.5 Hz, 1H), 6.97 - 6.89 (m, 1H), 6.74 (ddd, J=12.9, 8.4, 2.6 Hz, 1H), 5.32 (s, 1H), 4.21 (dd, J=18.6, 1.4 Hz, 1H), 3.91 (dd, J=18.6, 2.9 Hz, 1H), 1.86 (s, 3H), 1.34 (s, 9H).

Reference： [1]Patent: WO2014/98831,2014,A1 .Location in patent: Page/Page column 80; 81
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 8593 - 8600

23
[ 10325-70-9 ]
[ 58004-79-8 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 6572 - 6582
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 8529 - 8541

24
[ 10325-70-9 ]
2-(2-propylpyridin-4-yl)-4-(pyrimidin-5-yl)thiazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 6572 - 6582

25
N-(6-bromo-5-chloropyridin-2-yl)-4-(tert-butyl)benzenesulfonamide [ No CAS ]
[ 10325-70-9 ]
C₂₁H₂₁ClN₄O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 15h;Inert atmosphere;	A stirred solution of compound LXV (0.5 g; 1.24 mmol) and <strong>[10325-70-9]1-(pyrimidin-5-yl)ethan-1-one</strong>(LXXXIX; 0.6 g; 2.48 mmol) in 1,4-dioxane (40 ml) was purged with argon gas for 20minutes. To the reaction mixture was added 4,5 -bis(diphenylphosphino)-9,9-dimethylxanthene(0.57g, 0.992 mmol), palladium(II)acetate (0.11 g, 0.5 mmol) and potassium phosphate (0.73 g,3.47 mmol). The resultant solution was stirred at 100C for 15h. The reaction mixture wascooled, concentrated, and filtered through a celite bed. The crude reaction mass was dilutedwith water and extracted with ethyl acetate. The organic layer was washed with brine solutionand dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure followed bytrituration with hexane to obtain crude 4-(tert-butyl)-N-(5 -chloro-6-(2-oxo-2-(pyrimidin-5 -yl)ethyl)pyridin-2-yl)benzene sulfonamide XC, as a keto-enol tautomeric mixture. MS (M+1):445.2.

Reference： [1]Patent: WO2015/97122,2015,A1 .Location in patent: Page/Page column 127

26
N-(6-bromo-5-chloropyridin-2-yl)-4-(tert-butyl)benzenesulfonamide [ No CAS ]
[ 10325-70-9 ]
4-(tert-butyl)-N-(5-chloro-6-(2-(hydroxyimino)-2-(pyrimidin-5-yl)ethyl)pyridin-2-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.35 g		To a stirred solution of compound XC (1.5 g, tautomeric mixture) in methanol (60 ml) was added hydroxylamine hydrochloride (0.93 g; 13.51 mmol) followed by a 10% aqueous solution of sodium hydroxide (193m1). The resultant suspension was heated at 95C for 12 h and then cooled to room temperature. The reaction mixture was concentrated in vacuo and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution and dried over anhydrous Na2SO4, filtered and was evaporated under reduced pressure to obtain crude compound, which was purified by column chromatography using 18%ethyl acetate in hexane to afford the desired product (4-(tert-butyl)-N-(5-chloro-6-(2-(hydroxyimino)-2-(pyrimidin-5 -yl)ethyl)pyridin-2-yl)benzenesulfonamide as an off white solid(XCI; 0.35 g; 23% yield). ?H NMR (400 MHz, DMSO-d6) 6 11.90 (s, 1H), 11.03 (bs, 1H),9.11 (s, 1H), 8.95-8.87 (m, 2H), 7.73-7.69 (m, 3H), 7.53-7.48 (m, 2H), 6.82-6.80 (d,J=8.4 Hz,1H), 4.26 (s, 2H), 1.26 (s, 9H), MS (M+1): 460.1

Reference： [1]Patent: WO2015/97122,2015,A1 .Location in patent: Page/Page column 127; 128

27
[ 10325-70-9 ]
5-(1H-pyrazol-3-yl)pyrimidine [ No CAS ]

Reference： [1]Patent: US2015/322063,2015,A1

28
[ 10325-70-9 ]
5-(4-bromo-1H-pyrazol-3-yl)pyrimidine [ No CAS ]

Reference： [1]Patent: US2015/322063,2015,A1

29
[ 10325-70-9 ]
5-(4-bromo-1-methyl-1H-pyrazol-3-yl)pyrimidine [ No CAS ]

Reference： [1]Patent: US2015/322063,2015,A1

30
[ 10325-70-9 ]
7-((4-(4-chloro-3-(trifluoromethyl)phenoxy)benzyl)oxy)-2-(pyrimidin-5-yl)imidazo[1,2-a]pyrimidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8529 - 8541

31
[ 146374-27-8 ]
[ 10325-70-9 ]
2-methyl-N-[(1E)-1-(pyrimidin-5-yl)ethylidene]propane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) isopropylate; In dichloromethane; for 16h;Reflux;	2-Methyl-2-propanesulfinamide (2.73 g, 22.5 mmol) and Ti(OiPr)4 (1 1 .6 g, 40.9 mmol) were added to a solution of 1 -(5-pyrimidinyl)ethanone (2.5 g, 20.47 mmol) in DCM (100 mL) and the mixture was heated under reflux for 16 hrs. The mixture was cooled in an ice bath and diluted with anhydrous MeOH (20 mL) and aq. NaHCO3 (5 mL). The resulting suspension was stirred for 1 hr then filtered, washed through with EtOAC. The filtrate was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica gel column eluting with pet. Ether: EtOAc (100:0 to 50:50) to afford the title compound as a yellow oil, 3.2 g, 69%. (title compound was isolated in a ~85:15 mixture with 1 -(5-pyrimidinyl)ethanone, and the mixture was used as is in the next step). 1H NMR (400 MHz, CDCI3): delta 1 .32 (s, 9H), 2.80 (s, 3H), 9.15 (s, 2H), 9.28 (s, 1 H). LCMS m/ z= 226 [M+H]+

Reference： [1]Patent: WO2018/11681,2018,A1 .Location in patent: Page/Page column 102-103

32
[ 10325-70-9 ]
2-methyl-N-[1-(pyrimidin-5-yl)ethyl]propane-2-sulfinamide [ No CAS ]

Reference： [1]Patent: WO2018/11681,2018,A1

33
[ 10325-70-9 ]
C₁₄H₁₂N₂O [ No CAS ]