[ CAS No. 96833-41-9 ] {[proInfo.proName]}

Name: 96833-41-9|2-Chloro-4-methoxypyrimidin-5-amine|97%
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SKU: A152007
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Quality Control of [ 96833-41-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 96833-41-9 ]

Product Details of [ 96833-41-9 ]

CAS No. :	96833-41-9	MDL No. :	MFCD12402341
Formula :	C₅H₆ClN₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BTTZBKYSXZSBAS-UHFFFAOYSA-N
M.W :	159.57	Pubchem ID :	21186356
Synonyms :

Calculated chemistry of [ 96833-41-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.94
TPSA :	61.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.66
Log Po/w (XLOGP3) :	0.79
Log Po/w (WLOGP) :	0.73
Log Po/w (MLOGP) :	-0.25
Log Po/w (SILICOS-IT) :	0.86
Consensus Log Po/w :	0.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.71
Solubility :	3.15 mg/ml ; 0.0197 mol/l
Class :	Very soluble
Log S (Ali) :	-1.65
Solubility :	3.55 mg/ml ; 0.0223 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.02
Solubility :	1.51 mg/ml ; 0.00944 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.01

Safety of [ 96833-41-9 ]

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

Application In Synthesis of [ 96833-41-9 ]

* 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 [ 96833-41-9 ]
Downstream synthetic route of [ 96833-41-9 ]

[ 96833-41-9 ] Synthesis Path-Upstream 1~3

1
[ 5177-27-5 ]
[ 124-41-4 ]
[ 96833-41-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	at 20℃; for 1.5 h;	Preparation 164 2-Chloro-4-methoxypyrimidin-5-amine Sodium methoxide (0.5M in methanol, 3.7 mL, 1.829 mmol) was added to a solution of 2,4-dichloropyrimidin-5-amine (0.2 g, 1.220 mmol) in MeOH (2.5 mL). The reaction was stirred at room temperature for 1.5 hours. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na₂SO₄), filtered and concentrated under reduced pressure to afford the title product as a brown solid (177 mg, 91percent). ¹H NMR (500 MHz, CDCl₃): δ 3.93 (s, 3H), 5.31 (br s, 2H), 7.73 (s, 1H). LC (Method B)-MS (ESI, m/z) t_R 1.6 min, 160 [M+H]⁺
83%	at 0 - 20℃; for 66 h; Inert atmosphere	5.4Msodium methoxide (100 μ, 0.54 mmol) was added dropwise to a stirring solutionof 2,4-dichloropyrimidin-5 -amine (89 mg, 0.54 mmol) in methanol (2 mL) at 0 °Cunder nitrogen. The reaction was allowed to warm to room temperature andstirred for 1 hr. The reaction was treated with more 5.4M sodium methoxide (10μ) and stirred for a further 1 hr, then left to stand at room temperature for64 hrs. The reaction was quenched with acetic acid (1 mL) and concentrated invacuo. The residue was dissolved in EtOAc (20 mL) and washed with saturatedaqueous NaHC0₃ (2 x 6 mL), brine (6 mL), dried over Na₂SC>4,filtered and the filtrate was concentrated in vacuo. The residue obtained waspurified by flash column chromatography over silica (Biotage 10 g SNAPcartridge) eluting with heptane:EtOAc , smooth gradient 1 :0 to 7:3 to affordthe title compound as a white solid (80 mg, 83percent) ; H NMR (500 MHz,DMSO) δ 3.93 (s, 3H), 5.31 (s, 2H), 7.72 (s, 1H).
0.35 g	for 16 h; Reflux	A mixture of 2,4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25percent ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.

Reference： [1] Patent: US2013/345181, 2013, A1, . Location in patent: Paragraph 0785
[2] Patent: WO2014/184234, 2014, A1, . Location in patent: Page/Page column 71; 72
[3] Patent: WO2014/191632, 2014, A1, . Location in patent: Page/Page column 56

2
[ 67-56-1 ]
[ 5177-27-5 ]
[ 124-41-4 ]
[ 96833-41-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	at 20℃; for 1.5 h;	Preparation 164: 2-Chloro-4-methoxypyrimidin-5-amine; [00336] Sodium methoxide (0.5M in methanol, 3.7ml_, 1 .829mmol) was added to a solution of 2,4-dichloropyrimidin-5-amine (0.2g, 1 .220mmol) in MeOH (2.5ml_). The reaction was stirred at room temperature for 1 .5 hours. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na₂S0₄), filtered and concentrated under reduced pressure to afford the title product as a brown solid (177mg, 91 percent).¹ H NMR (500MHz, CDCI₃): δ 3.93 (s, 3H), 5.31 (br s, 2H), 7.73 (s, 1 H). LC (Method B)-MS (ESI, m/z) f_R 1 .6 min, 160 [M+H]⁺

Reference： [1] Patent: WO2012/123745, 2012, A1, . Location in patent: Page/Page column 117

3
[ 5177-27-5 ]
[ 96833-41-9 ]

Reference： [1] Patent: US5861401, 1999, A,

[ 96833-41-9 ] Synthesis Path-Downstream 1~11

Yield	Reaction Conditions	Operation in experiment
		A. To a solution of 2-chloro-4-methoxy-6-methyl-5-nitropyrimidine (1.01 g, 5.00 mmol) in THF (20 mL) and water (20 mL) is added sodium hydrosulfite (8.6 g, 50.0 mmol). The mixture is stirred at room temperature for 2.5 h, diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. Combined extracts are washed with brine, dried (sodium sulfate), filtered and concentrated to give 2-chloro-4-methoxypyrimidine-5-ylamine (600 mg): 1H NMR (CDCl3, 400 MHz) delta2.38 (s, 3H), 4.02 (s, 3H).
171 mg	In methanol; for 16.0h;Reflux;	General procedure: 2-Chloro-4-methoxypyrimidin-5-amine 2-Chloro-4-methoxypyrimidin-5-amine was synthesized using the same method as described for 5-bromo-3-methoxypyrazin-2-amine in Example 2. 200 mg (1.2 mmol) of dichloropyrimidin-5-amine, 263 mg (4.9 mmol) of sodium methoxide, and 30 ml of methanol was used. Yield: 171 mg 1H NMR (CDCI3): 4.04 (3H, s), 7.76 (1H, s)

2
[ 96833-41-9 ]
[ 123-38-6 ]
(2-chloro-4-methoxy-6-methylpyrimidine-5-yl)-dipropylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In acetic acid; 1,2-dichloro-ethane;	B. To a solution of <strong>[96833-41-9]2-chloro-4-methoxypyrimidine-5-ylamine</strong> (400 mg, 2.3 mmol) in 1,2-dichloroethane (60 mL) is added propionaldehyde (700 mg, 12 mmol) and glacial acetic acid (660 mg). After 10 minutes sodium triacetoxyborohydride (2.5g, 12 mmol) is added in one portion. After 3 h the volatiles are removed by rotary evaporation. The residue is partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, the layers are separated and the aqueous layer further extracted with ethyl acetate. The combined organics are washed with water, brine, dried (sodium sulfate), filtered and concentrated to give (2-chloro-4-methoxy-6-methylpyrimidine-5-yl) dipropylamine (566 mg): 1H NMR (CDCl3, 400 MHz) delta0.85 (t, 6H), 1.3 (m, 4H), 2.4 (s, 3H), 2.82 (t, 4H), 4.0 (s, 3H); MS (CI) 258.

Reference： [1]Patent: US2002/72521,2002,A1

3
[ 96833-41-9 ]
[ 605-65-2 ]
5-dimethylamino-N-(2-chloro-4-methoxy-5-pyrimidinyl)-1-naphthalenesulphonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dimethoxyethane;	EXAMPLE 34 Sodium hydride (60% dispersion in oil; 0.1 g) was added to a solution of <strong>[96833-41-9]5-amino-2-chloro-4-methoxypyrimidine</strong> (0.159 g) in 1,2-dimethoxyethane (10 ml). When evolution of hydrogen had ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (0.336 g) was added and the solution was stirred for 2 hours. Volatile material was then removed by evaporation. The residue was purified by elution with ethyl acetate/hexane/acetic acid (0-20% ethyl acetate, 0.1% acetic acid) through a silica gel Mega Bond Elut column to give 5-dimethylamino-N-(2-chloro-4-methoxy-5-pyrimidinyl)-1-naphthalenesulphonamide (0.067 g) as an oil; 1 H NMR (d6 -DMSO): 2.85 (s, 6H), 3.39 (s, 3H), 7.3 (d, 1H), 7.6 (t of t, 2H), 8.08 (d, 1H), 8.25 (s, 1H), 8.30 (d, 1H), 8.5 (d, 1H), 10.42 (s, 1H); mass spectrum (+ve FAB, dichloromethane/NBA): 393 (M+H)+.

Reference： [1]Patent: US5861401,1999,A

4
[ 5177-27-5 ]
[ 96833-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; sodium; In methanol; water;	(i) A mixture of <strong>[5177-27-5]5-amino-2,4-dichloropyrimidine</strong> (0.32 g) (obtained as described in Chem. Pharm. Bull., (JAPAN), 1958, 6, 343-346) and a solution of sodium methoxide in methanol (from sodium (0.05 g) and methanol (25 ml)) was heated at reflux for 15 minutes and allowed to cool. Volatile material was removed by evaporation and a small volume of water added. The mixture was extracted twice with ether and the combined extracts were dried (MgSO4) and evaporated to give 5-amino-2-chloro-4-methoxypyrimidine (0.2 g) as an oil; 1 H NMR (d6 -DMSO): 3.92 (s, 3H), 5.25 (s, 2H), 7.72 (s, 1H); mass spectrum (+ve CI): 160 (M+H)+.

Reference： [1]Patent: US5861401,1999,A

5
[ 67-56-1 ]
[ 5177-27-5 ]
[ 124-41-4 ]
[ 96833-41-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	at 20℃; for 1.5h;	Preparation 164: 2-Chloro-4-methoxypyrimidin-5-amine; [00336] Sodium methoxide (0.5M in methanol, 3.7ml_, 1 .829mmol) was added to a solution of <strong>[5177-27-5]2,4-dichloropyrimidin-5-amine</strong> (0.2g, 1 .220mmol) in MeOH (2.5ml_). The reaction was stirred at room temperature for 1 .5 hours. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure to afford the title product as a brown solid (177mg, 91 %).1 H NMR (500MHz, CDCI3): delta 3.93 (s, 3H), 5.31 (br s, 2H), 7.73 (s, 1 H). LC (Method B)-MS (ESI, m/z) fR 1 .6 min, 160 [M+H]+

Reference： [1]Patent: WO2012/123745,2012,A1 .Location in patent: Page/Page column 117

6
[ 96833-41-9 ]
[ 761446-44-0 ]
[ 1400287-40-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In methanol; 1,2-dimethoxyethane; at 150℃; for 0.166667h;Microwave irradiation;	Preparation 119: 4-Methoxy-2-(1 -methyl-1 H-pyrazol-4-yl)pyrimidin-5-amine; [00289] Tetrakis(triphenylphosphine)palladium (30mg, 0.026mmol) was added to a solution of <strong>[96833-41-9]2-chloro-4-methoxypyrimidin-5-amine</strong> (41 mg, 0.257mmol), 1 -methyl-4- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (107mg, 0.514mmol) and cesium fluoride (1 17mg, 0.771 mmol) in DME/MeOH (2/1 , 1 .6ml_). The reaction mixture was heated under microwave irradiation at ~ 50 C for 10 minutes. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with DCM/EtOH 99/1 to 90/10 followed by filtration through a SCX-2 column to afford the title product as a white solid (49mg, 93%).1 H NMR (500MHz, CDCI3): delta 3.68 (br s, 2H), 3.93 (s, 3H), 4.06 (s, 3H), 7.88 (s, 1 H), 7.92 (s, 1 H), 8.04 (s, 1 H). LC (Method B)-MS (ESI, m/z) fR 1 .33 min, 206 [M+H]+
93%	With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 150℃; for 0.166667h;Microwave irradiation;	Preparation 119 4-Methoxy-2-(1-methyl-1H-pyrazol-4-yl)pyrimidin-5-amine Tetrakis(triphenylphosphine)palladium (30 mg, 0.026 mmol) was added to a solution of <strong>[96833-41-9]2-chloro-4-methoxypyrimidin-5-amine</strong> (41 mg, 0.257 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (107 mg, 0.514 mmol) and cesium fluoride (117 mg, 0.771 mmol) in DME/MeOH (2/1, 1.6 mL). The reaction mixture was heated under microwave irradiation at 150 C. for 10 minutes. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with DCM/EtOH 99/1 to 90/10 followed by filtration through a SCX-2 column to afford the title product as a white solid (49 mg, 93%). 1H NMR (500 MHz, CDCl3): delta 3.68 (br s, 2H), 3.93 (s, 3H), 4.06 (s, 3H), 7.88 (s, 1H), 7.92 (s, 1H), 8.04 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 1.33 min, 206 [M+H]+

Reference： [1]Patent: WO2012/123745,2012,A1 .Location in patent: Page/Page column 101
[2]Patent: US2013/345181,2013,A1 .Location in patent: Paragraph 0733

7
[ 5177-27-5 ]
[ 124-41-4 ]
[ 96833-41-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With methanol; at 20℃; for 1.5h;	Preparation 164 2-Chloro-4-methoxypyrimidin-5-amine Sodium methoxide (0.5M in methanol, 3.7 mL, 1.829 mmol) was added to a solution of <strong>[5177-27-5]2,4-dichloropyrimidin-5-amine</strong> (0.2 g, 1.220 mmol) in MeOH (2.5 mL). The reaction was stirred at room temperature for 1.5 hours. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to afford the title product as a brown solid (177 mg, 91%). 1H NMR (500 MHz, CDCl3): delta 3.93 (s, 3H), 5.31 (br s, 2H), 7.73 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 1.6 min, 160 [M+H]+
83%	In methanol; at 0 - 20℃; for 66h;Inert atmosphere;	5.4Msodium methoxide (100 mu, 0.54 mmol) was added dropwise to a stirring solutionof 2,4-dichloropyrimidin-5 -amine (89 mg, 0.54 mmol) in methanol (2 mL) at 0 Cunder nitrogen. The reaction was allowed to warm to room temperature andstirred for 1 hr. The reaction was treated with more 5.4M sodium methoxide (10mu) and stirred for a further 1 hr, then left to stand at room temperature for64 hrs. The reaction was quenched with acetic acid (1 mL) and concentrated invacuo. The residue was dissolved in EtOAc (20 mL) and washed with saturatedaqueous NaHC03 (2 x 6 mL), brine (6 mL), dried over Na2SC>4,filtered and the filtrate was concentrated in vacuo. The residue obtained waspurified by flash column chromatography over silica (Biotage 10 g SNAPcartridge) eluting with heptane:EtOAc , smooth gradient 1 :0 to 7:3 to affordthe title compound as a white solid (80 mg, 83%) ; H NMR (500 MHz,DMSO) delta 3.93 (s, 3H), 5.31 (s, 2H), 7.72 (s, 1H).
0.35 g	In methanol; for 16h;Reflux;	A mixture of <strong>[5177-27-5]2,4-dichloropyrimidin-5-amine</strong> (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25% ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.

Reference： [1]Patent: US2013/345181,2013,A1 .Location in patent: Paragraph 0785
[2]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 71; 72
[3]Patent: WO2014/191632,2014,A1 .Location in patent: Page/Page column 56

8
[ 96833-41-9 ]
[ 719-22-2 ]
[ 1608498-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; aluminum (III) chloride; In 1,2-dichloro-ethane; for 48.0h;Reflux;	2,6-Di-tert-butyl-4-[(2-chloro-4-methoxypyrimidin-5-yl)amino]phenol was synthesized using the same method as described for 4-[(5-bromo-3-methoxypyrazin-2-yl)amino]-2,6-di- tert-butylphenol in Example 2. 358 mg (2.67 mmol) of A1C13, 0.51 ml of pyridine, 20 ml of 1,2-dichloroethane, 235 mg (1.07 mmol) of 2,6-di-tert-butyl-l,4-benzoquinone, and 170 mg (1.07 mmol) of <strong>[96833-41-9]2-chloro-4-methoxypyrimidin-5-amine</strong> was used. Reaction time in the imine formation stage was 48 h.

Reference： [1]Patent: WO2014/68171,2014,A1 .Location in patent: Page/Page column 28

9
[ 96833-41-9 ]
4-bromo-2-chloro-6-methoxypyrimidin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60 mg	With N-Bromosuccinimide; In chloroform; at 20℃; for 3.0h;	N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of <strong>[96833-41-9]2-chloro-4-methoxypyrimidin-5-amine</strong> (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.

Reference： [1]Patent: WO2014/191632,2014,A1 .Location in patent: Page/Page column 57

10
[ 96833-41-9 ]
[ 163295-70-3 ]
N-(2-chloro-4-methoxypyrimidin-5-yl)-1-(3,5-dichlorophenyl)methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 22.0h;	(3,5-dichlorophenyl)methanesulfonyl chloride (128 mg, 0.49 mmol) was added to a solution of <strong>[96833-41-9]2-chloro-4-methoxypyrimidin-5-amine</strong> (75 mg, 0.47 mmol) and DIPEA (123 mu, 0.71 mmol) in DCM (2 mL). The reaction was allowed to stir at room temperature for 18 hrs. The reaction was treated with more (3,5-dichlorophenyl)methanesulfonyl chloride (20 mg, 0.08 mmol) and stirred for a further 4 hrs. The reaction was diluted with DCM (15 mL), washed with saturated aqueous citric acid (2 x 6 mL), sat. aq. NaHC03 (2 x 6 mL), brine (6 mL), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue obtained was purified by flash column chromatography over silica (Biotage 10 g SNAP cartridge) eluting with Heptane:EtOAc constant gradient 1 :0 to 7:3 to afford the title compound (108 mg, 60 %) as a white solid; m z=381.8, 383.9 (MH)+.

Reference： [1]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 72

11
[ 96833-41-9 ]
[ 287944-16-5 ]
C₁₀H₁₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 90℃; for 4.0h;Inert atmosphere; Schlenk technique;	In a Shlenck reactor, a solution of 6-chloro-2-methoxy-3-nitropyridine (1.00 g, 5.30mmol), 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester (1.23 g, 5.83 mmol) andK3P04 (3.38 g, 15.90 mmol) in 1,4-dioxane (44 mL) and distilled water (9 mL) was degassed under N2. [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium (II), complex with dichloromethane (434.00 mg, 0.53 mmol) was added, the mixture was degassed again under N2 and heated at 80 C for 4 h. The mixture was extended withEtOAc and filtered on a pad of celite. The cake was washed with EtOAc and water. The layers were separated and the organic layer was dried over Mg504, filtered off and evaporated in vacuo to give a brown solid. The residue was purified by column chromatography on silica gel (irregular SiOH, 15-40 jim, 50 g, dry loading on celite, mobile phase: heptane/EtOAc, gradient: 95:5 to 60:40) to give 922 mg of intermediate138 (74% yield, yellow solid).

Reference： [1]Patent: WO2017/125534,2017,A1 .Location in patent: Page/Page column 268; 269

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[ 55150-17-9 ]

4-Ethoxypyrimidin-5-amine

Similarity: 0.79

[ 53135-45-8 ]

4-Methoxy-2-methylpyrimidin-5-amine

Similarity: 0.73

[ 14048-15-8 ]

2,4-Dimethoxypyrimidin-5-amine

Similarity: 0.71

[ 56621-90-0 ]

5-Amino-2-chloropyrimidine

Similarity: 0.70

[ 943314-62-3 ]

3-((2-Chloropyrimidin-4-yl)oxy)aniline

Similarity: 0.68

Related Parent Nucleus of
[ 96833-41-9 ]

Pyrimidines

[ 22536-63-6 ]

2-Chloro-4-methoxypyrimidine

Similarity: 0.83

[ 55150-17-9 ]

4-Ethoxypyrimidin-5-amine

Similarity: 0.79

[ 22536-64-7 ]

2-Chloro-4-methoxy-6-methylpyrimidine

Similarity: 0.78

[ 1445894-94-9 ]

2-Chloro-4-isopropoxy-5-nitropyrimidine

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[ 53135-45-8 ]

4-Methoxy-2-methylpyrimidin-5-amine

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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

[ CAS No. 96833-41-9 ] {[proInfo.proName]}

Quality Control of [ 96833-41-9 ]

Related Doc. of [ 96833-41-9 ]

Product Details of [ 96833-41-9 ]

Calculated chemistry of [ 96833-41-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 96833-41-9 ]

Application In Synthesis of [ 96833-41-9 ]

[ 96833-41-9 ] Synthesis Path-Upstream 1~3

[ 96833-41-9 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 96833-41-9 ]

Chlorides

Ethers

Amines

Related Parent Nucleus of [ 96833-41-9 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 96833-41-9 ]

Related Parent Nucleus of
[ 96833-41-9 ]