[ CAS No. 1439-09-4 ]

Name: 1439-09-4|5-Bromo-4-methylpyrimidine|98%
Brand: Ambeed
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Quality Control of [ 1439-09-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1439-09-4 ]

Product Details of [ 1439-09-4 ]

CAS No. :	1439-09-4	MDL No. :	MFCD10000597
Formula :	C₅H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ALRPHTZYJPXPGN-UHFFFAOYSA-N
M.W :	173.01	Pubchem ID :	12461863
Synonyms :

Calculated chemistry of [ 1439-09-4 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.7
TPSA :	25.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	1.29
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	0.72
Log Po/w (SILICOS-IT) :	2.08
Consensus Log Po/w :	1.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.28
Solubility :	0.907 mg/ml ; 0.00524 mol/l
Class :	Soluble
Log S (Ali) :	-1.43
Solubility :	6.41 mg/ml ; 0.037 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.89
Solubility :	0.224 mg/ml ; 0.0013 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.33

Safety of [ 1439-09-4 ]

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 [ 1439-09-4 ]

* 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 [ 1439-09-4 ]
Downstream synthetic route of [ 1439-09-4 ]

[ 1439-09-4 ] Synthesis Path-Upstream 1~2

1
[ 4595-59-9 ]
[ 917-54-4 ]
[ 1439-09-4 ]

Yield	Reaction Conditions	Operation in experiment
15%	Stage #1: at 20℃; for 1 h; Stage #2: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; diethyl ether at 20℃; for 16 h;	To 5-bromopyrimidine (17.3 g, 109 mmol) in diethyl ether (100 mL) , methyllithium in diethyl ether (109 mmol, 1.09 M, 100 mL) was gradually added dropwise at room temperature, and the resulting reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was stirred with water (1.96 mL, 109 mmol) and 2 , 3-dichloro-5 , 6-dicyano-p- benzoquinone (24.7 g, 109 mmol) in tetrahydrofuran (150 mL) at room temperature for 16 hours. After completion of the reaction, water and ethyl acetate were added, and the organic layer was separated. The organic layer was washed with IM aqueous sodium hydroxide, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1) to give the desired product (2.9 g, 15percent yield) . Morphology: yellow oil 1H-NMR(CDCl₃) δ :2.65 (s, 3H), 8.72 (s, 1H), 8.98 (s, 1H)

Reference： [1] Patent: WO2009/57827, 2009, A1, . Location in patent: Page/Page column 167

2
[ 3438-55-9 ]
[ 1439-09-4 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 8, p. 3119 - 3126

[ 1439-09-4 ] Synthesis Path-Downstream 1~61

1
[ 1439-09-4 ]
[ 19175-07-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

2
[ 1439-09-4 ]
[ 114969-56-1 ]
[ 114970-00-2 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

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[ 3438-55-9 ]
[ 1439-09-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

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Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

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[ 114969-98-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

8
[ 1439-09-4 ]
[ 114969-54-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

9
[ 1439-09-4 ]
[ 114969-85-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

10
[ 1439-09-4 ]
[ 114969-83-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

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[ 114969-78-7 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3119 - 3126

12
[4-(3-dihydroxyboranyl-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 1439-09-4 ]
(imino-{4-[3-(4-methyl-pyrimidin-5-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium carbonate; triethylamine;bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; ethanol; toluene; at 90℃; for 2.25h;	To a flask with a reflux condenser under argon was added 5-Bromo-4-methyl-pyrimidine (9 mg, 0.044 MMOL), prepared according to the procedure of Yamanaka, SAKAMOTO, Nishimura, and Sagi, Chem. Pharm. Bull. 35 (8), 3119-3126 (1987). [4-(3-dihydroxyboranyl-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-CARBAMIC acid tert-butyl ester (20 mg, 0.044 mmol, Example 140 : step a), Na2C03 (2M, 0.220 mL, 0.44 mmol), Pd (PPh3) 4 (8 mg, 0.007 mmol), ethanol (0.220 mL) and toluene (0.440 mL). PDCL2 (PPh3) 2 (42 mg, 0.06 mmol), dioxane (4 mL), and triethylamine (420 L, 3 mmol) and the mixture was stirred for 2 h 15 min at 90 oC. After cooling to rt, EtOAc (2 mL) and NAHC03 (saturated, 2 mL) were added and the layers were separated. The organic layer concentrated in vacuo followed by purification of the crude material by preparative TLC (5% methanol in dichloromethane) to yield the title compound (19 mg, 87%) as a white solid. 1H-NMR (CDC13) : delta 9.12 (s, 1H), 8.54 (s, 1H), 8.10-7. 29 (m, 7H), 2.59 (s, 3H), 2.50 (s, 3H), 1.51 (s, 9H). ESI-MS (m/z): Calcd. for C22H24N404S3 : 504.1 (M-BOC) +H ; found : 405. 1.

Reference： [1]Patent: WO2003/99805,2003,A1 .Location in patent: Page 397

13
[4-(3-Dihydroxyboranyl-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 1439-09-4 ]
(imino-{4-[3-(4-methyl-pyrimidin-5-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydrogencarbonate; sodium carbonate; triethylamine;Pd(PPh3)4; PdCl2(PPh3)2; In 1,4-dioxane; methanol; ethanol; dichloromethane; ethyl acetate; toluene;	a (Imino-{4-[3-(4-methyl-pyrimidin-5-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester To a flask with a reflux condenser under argon was added 5-Bromo-4-methyl-pyrimidine (9 mg, 0.044 mmol), prepared according to the procedure of Yamanaka, Sakamoto, Nishimura, and Sagi, Chem. Pharm. Bull. 35(8), 3119-3126 (1987). [4-(3-dihydroxyboranyl-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (20 mg, 0.044 mmol, Example 140: step a), Na2CO3 (2M, 0.220 mL, 0.44 mmol), Pd(PPh3)4 (8 mg, 0.007 mmol), ethanol (0.220 mL) and toluene (0.440 mL). PdCl2(PPh3)2 (42 mg, 0.06 mmol), dioxane (4 mL), and triethylamine (420 muL, 3 mmol) and the mixture was stirred for 2 h 15 min at 90 C. After cooling to rt, EtOAc (2 mL) and NaHCO3 (saturated, 2 mL) were added and the layers were separated. The organic layer concentrated in vacuo followed by purification of the crude material by preparative TLC (5% methanol in dichloromethane) to yield the title compound (19 mg, 87%) as a white solid. 1H-NMR (CDCl3): delta 9.12 (s, 1H), 8.54 (s, 1H), 8.10-7.29 (m, 7H), 2.59 (s, 3H), 2.50 (s, 3H), 1.51 (s, 9H). ESI-MS (m/z): Calcd. for C22H24N4O4S3: 504.1 (M-BOC)+H; found: 405.1.

Reference： [1]Patent: US2004/9995,2004,A1

14
[ 4595-59-9 ]
[ 917-54-4 ]
[ 1439-09-4 ]

Yield	Reaction Conditions	Operation in experiment
15%		To 5-bromopyrimidine (17.3 g, 109 mmol) in diethyl ether (100 mL) , methyllithium in diethyl ether (109 mmol, 1.09 M, 100 mL) was gradually added dropwise at room temperature, and the resulting reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was stirred with water (1.96 mL, 109 mmol) and 2 , 3-dichloro-5 , 6-dicyano-p- benzoquinone (24.7 g, 109 mmol) in tetrahydrofuran (150 mL) at room temperature for 16 hours. After completion of the reaction, water and ethyl acetate were added, and the organic layer was separated. The organic layer was washed with IM aqueous sodium hydroxide, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1) to give the desired product (2.9 g, 15% yield) . Morphology: yellow oil 1H-NMR(CDCl3) delta :2.65 (s, 3H), 8.72 (s, 1H), 8.98 (s, 1H)

Reference： [1]Patent: WO2009/57827,2009,A1 .Location in patent: Page/Page column 167

15
[ 1439-09-4 ]
5-bromo-4-bromomethylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 16h;Reflux;	N-Bromosuccinimide (5.96 g, 31.8 mmol) and azobisisobutyronitrile (0.50 g, 2.9 mmol) were added to asolution of <strong>[1439-09-4]5-bromo-4-methyl-pyrimidine</strong> (5 g, 29 mmol) in carbon tetrachloride (72 ml). The resultingmixture was heated at reflux for 16 hours, then allowed to cool and filtered. The solid was washed with dichloromethane and the filtrate concentrated under reduced pressure to leave a residue which was purified by silica gel chromatography (gradient elution: 5 - 100% ethyl acetate in iso-hexane)to provide 5- bromo-4-bromomethylpyrimidine (4.22 g, 58%).Characterising data for the compound are as follows: 1H NMR (400 MHz, CDCI3) oe 9.10 (s, 1 H), 8.84 (s,1H) and 4.57 (s, 2H) ppm.
	With bromine; acetic acid; at 80℃; for 0.666667h;	5-Bromo-4-methylpyrimidine (2.90 g, 16.8 mmol) in acetic acid (40 mL) was stirred with bromine (3.18 g, 20.2 mmol) at 80C for 40 minutes. After completion of <n="170"/>the reaction, the reaction solution was cooled, diluted with ethyl acetate and neutralized with water and 1 M aqueous sodium hydroxide, and the organic layer was separated, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate = 7/1)

Reference： [1]Patent: WO2015/4282,2015,A1 .Location in patent: Page/Page column 71
[2]Patent: WO2009/57827,2009,A1 .Location in patent: Page/Page column 167-168

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[ 1353577-91-9 ]