[ CAS No. 933702-55-7 ] {[proInfo.proName]}

Name: 933702-55-7|2-Chloropyrimidine-5-carbaldehyde|95%
Brand: Ambeed
SKU: A217564
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Quality Control of [ 933702-55-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 933702-55-7 ]

Product Details of [ 933702-55-7 ]

CAS No. :	933702-55-7	MDL No. :	MFCD10696891
Formula :	C₅H₃ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LJYQVOPFBNMTKJ-UHFFFAOYSA-N
M.W :	142.54	Pubchem ID :	21698350
Synonyms :

Calculated chemistry of [ 933702-55-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.43
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) :	-6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.07
Log Po/w (XLOGP3) :	0.63
Log Po/w (WLOGP) :	0.94
Log Po/w (MLOGP) :	-0.43
Log Po/w (SILICOS-IT) :	1.72
Consensus Log Po/w :	0.79

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.55
Solubility :	4.04 mg/ml ; 0.0283 mol/l
Class :	Very soluble
Log S (Ali) :	-1.1
Solubility :	11.2 mg/ml ; 0.0786 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.19
Solubility :	0.916 mg/ml ; 0.00643 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 933702-55-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 933702-55-7 ]

* 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 [ 933702-55-7 ]
Downstream synthetic route of [ 933702-55-7 ]

[ 933702-55-7 ] Synthesis Path-Upstream 1~6

1
[ 933702-55-7 ]
[ 120747-84-4 ]

Reference： [1] Patent: TW2018/29406, 2018, A, . Location in patent: Page/Page column 32-33

2
[ 933702-55-7 ]
[ 55551-49-0 ]

Yield	Reaction Conditions	Operation in experiment
97.7%	With triethylamine In tetrahydrofuran; 1,4-dioxane	2-(Dimethylamino)pyrimidine-5-carbaldehyde 2-Chloropyrimidine-5-carbaldehyde (412 mg, 2.89 mmol) and Et₃N (482 uL, 3.47 mmol) were dissolved in dioxane (20 mL) and a solution of Me₂NH in THF (1.59 mL, 2.0M, 3.18 mmol) was added. The reaction mixture was stirred for 1 h, filtered, washed with dioxane (5 mL), and concentrated in vacuo to give the title compound (427 mg, 97.7percent) as a yellow solid. LCMS (ES⁺): 152.2 [MH]⁺. HPLC: Rt 4.14 min, 97.9percent purity.

Reference： [1] Patent: US2015/258101, 2015, A1,

3
[ 933702-55-7 ]
[ 124-40-3 ]
[ 55551-49-0 ]

Yield	Reaction Conditions	Operation in experiment
97.7%	With triethylamine In tetrahydrofuran; 1,4-dioxane for 1 h;	INTERMEDIATE 64 2-(Dimethylamino)pyrimidine-5-carbaldeh de 2-Chloropyrimidine-5-carbaldehyde (412mg, 2.89mmol) and Et₃N (482uL, 3.47mmol) were dissolved in dioxane (20mL) and a solution of Me₂NH in THF (1.59mL, 2.0M, 3.18mmol) was added. The reaction mixture was stirred for 1 h, filtered, washed with dioxane (5mL), and concentrated in vacuo to give the title compound (427mg, 97.7percent) as a yellow solid. LCMS (ES⁺): 152.2 [MH]⁺. HPLC: Rt 4.14min, 97.9percent purity.

Reference： [1] Patent: WO2014/140592, 2014, A1, . Location in patent: Page/Page column 43

4
[ 131467-06-6 ]
[ 933702-55-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide In 1,4-dioxane; water at 20℃;	To a solution of 2-chloro-5-vinylpyrimidine (O.lg, 0.7 mmol) in dioxane (ImL) and water (ImL) was added 2,6-lutidine (0.188g, 1.76 mmol) followed by the addition of osmium tetroxide (3.5mg, 0.007 mmol) and sodium periodate (0.59g, 2.81 mmol). Stirred the reaction mass for 2- 3h at room temperature. Then quenched with ethyl acetate and water. The ethyl acetate layer was washed with water followed by brine. Dried and concentrated the organic layer under vacuum. The residue was purified by column chromatography by eluting with a 20percent ethyl acetate -hexane system to afford the title compound (0.04g, 40percent ). ¹HNMR (CDC1₃, 300MHz): δ 10.15 (s, 1H), 9.07 (s, 2H).

Reference： [1] Patent: WO2016/164703, 2016, A1, . Location in patent: Page/Page column 60; 61

5
[ 1046816-75-4 ]
[ 933702-55-7 ]

Reference： [1] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0231

6
[ 32779-36-5 ]
[ 109-94-4 ]
[ 933702-55-7 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 42, p. 11199 - 11202[2] Angew. Chem., 2014, vol. 126, # 42, p. 11381 - 11384,4
[3] Patent: WO2017/136450, 2017, A2, . Location in patent: Sheet 105/122
[4] Patent: WO2018/6074, 2018, A2, . Location in patent: Paragraph 0076; 00629

[ 933702-55-7 ] Synthesis Path-Downstream 1~45

1
[ 933702-55-7 ]
[ 1354496-02-8 ]

Reference： [1]Patent: US2013/109653,2013,A1

2
[ 933702-55-7 ]
[ 1354495-70-7 ]
[ 1354495-76-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1-methyl-pyrrolidin-2-one; at 20℃; for 3.08h;	To a solution of 1.00 g (1.48 mmol) of (-)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 10, in 5 ml of 1-methyl-2-pyrrolidone, 0.23 g (1.6 mmol) of <strong>[933702-55-7]2-chloro-5-formyl pyrimidine</strong> and 265 mul (1.78 mmol) of diazabicycloundecene were added, and the reaction solution was stirred at room temperature for 1 hour. Then, 0.023 g (0.16 mmol) of <strong>[933702-55-7]2-chloro-5-formyl pyrimidine</strong> was added thereto and the reaction solution was further stirred at room temperature for 0.58 hours. Furthermore, 0.023 g (0.16 mmol) of <strong>[933702-55-7]2-chloro-5-formyl pyrimidine</strong> was added thereto and the reaction solution was stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction solution was poured into saturated sodium hydrogencarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=40/10 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 1.00 g of the title compound as a light yellow solid (yield: 87%). 1H-NMR spectrum (300 MHz, CDCl3) delta ppm: 9.71 (1H, s), 8.65 (2H, s), 7.63 (2H, d, J=8 Hz), 7.37 (2H, d, J=8 Hz), 7.25 (2H, d, J=9 Hz), 7.16 (1H, d, J=48 Hz), 6.87 (2H, d, J=9 Hz), 5.03-4.91 (1H, m), 4.83 (1H, t, J=5 Hz), 4.81 (1H, d, J=11 Hz), 4.77-4.67 (1H, m), 4.39 (1H, d, J=11 Hz), 3.79 (3H, s), 3.25-3.09 (1H, m), 2.92-2.74 (2H, m), 2.84 (1H, d, J=17 Hz), 2.65 (1H, d, J=17 Hz), 2.34-1.46 (14H, m), 1.19 (3H, s), 1.03 (3H, s), 0.79-0.68 (1H, m). Mass spectrum (EI, m/z): 780 [M+].

Reference： [1]Patent: US2013/109653,2013,A1 .Location in patent: Paragraph 0757-0760

3
[ 933702-55-7 ]
[ 128622-15-1 ]
[ 1354496-03-9 ]

Yield	Reaction Conditions	Operation in experiment
		2401-2403, in 16 ml of tetrahydrofuran was cooled to 0 C. and 1.6 ml (2.6 mmol) of 1.7 N n-butyl lithium/n-hexane solution was added thereto, and the reaction solution was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0 C. again and then a solution of 0.31 g (2.2 mmol) of <strong>[933702-55-7]2-chloropyrimidin-5-carbaldehyde</strong> in 4 ml of tetrahydrofuran was added to the reaction solution, and the reaction solution was stirred at room temperature for 30 minutes. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=100/0-80/20 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 0.17 g of 2-chloro-5-(4,4,4-trifluoro-1-buten-1-yl)pyrimidine.

Reference： [1]Patent: US2013/109653,2013,A1 .Location in patent: Paragraph 0797-0798

4
[ 933702-55-7 ]
[ 124-40-3 ]
[ 55551-49-0 ]

Yield	Reaction Conditions	Operation in experiment
97.7%	With triethylamine; In tetrahydrofuran; 1,4-dioxane; for 1h;	INTERMEDIATE 64 2-(Dimethylamino)pyrimidine-5-carbaldeh de 2-Chloropyrimidine-5-carbaldehyde (412mg, 2.89mmol) and Et3N (482uL, 3.47mmol) were dissolved in dioxane (20mL) and a solution of Me2NH in THF (1.59mL, 2.0M, 3.18mmol) was added. The reaction mixture was stirred for 1 h, filtered, washed with dioxane (5mL), and concentrated in vacuo to give the title compound (427mg, 97.7%) as a yellow solid. LCMS (ES+): 152.2 [MH]+. HPLC: Rt 4.14min, 97.9% purity.

Reference： [1]Patent: WO2014/140592,2014,A1 .Location in patent: Page/Page column 43

5
[ 933702-55-7 ]
4-((1R,2R)-2-(((2-fluoro-4-(methylsulfonyl)benzyl)oxy)methyl)cyclopropyl)piperidine hydrochloride [ No CAS ]
[ 1416365-05-3 ]