[ CAS No. 34171-40-9 ] {[proInfo.proName]}

Name: 34171-40-9|2,4-Dichloro-5-ethylpyrimidine|97%
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SKU: A213378
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Quality Control of [ 34171-40-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 34171-40-9 ]

SDS Specification

Alternatived Products of [ 34171-40-9 ]

Product Details of [ 34171-40-9 ]

CAS No. :	34171-40-9	MDL No. :	MFCD11040247
Formula :	C₆H₆Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YFYFVWTWMBQHOH-UHFFFAOYSA-N
M.W :	177.03	Pubchem ID :	10012458
Synonyms :

Calculated chemistry of [ 34171-40-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.83
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) :	-5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.19
Log Po/w (XLOGP3) :	2.92
Log Po/w (WLOGP) :	2.35
Log Po/w (MLOGP) :	1.49
Log Po/w (SILICOS-IT) :	2.92
Consensus Log Po/w :	2.37

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.16
Solubility :	0.124 mg/ml ; 0.0007 mol/l
Class :	Soluble
Log S (Ali) :	-3.12
Solubility :	0.133 mg/ml ; 0.000754 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.67
Solubility :	0.0375 mg/ml ; 0.000212 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.84

Safety of [ 34171-40-9 ]

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

Application In Synthesis of [ 34171-40-9 ]

* 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 [ 34171-40-9 ]
Downstream synthetic route of [ 34171-40-9 ]

[ 34171-40-9 ] Synthesis Path-Upstream 1~3

1
[ 4212-49-1 ]
[ 34171-40-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 120℃; for 5 h;	Step A: Synthesis of 2,4-dichloro-5-ethylpyrimidine. To a suspension of 5-ethyluracil (1 g, 7.1 mmol) in POCl₃ (4.5 mL) was slowly added N,N-dimethylaniline (1 mL). The reaction was heated at reflux (~120 °C) for 5 h until the starting material was completely dissolved and the entire solution turned a purple color. The mixture was allowed to cool and poured very slowly into ice (~40 g). The resulting ppt was filtered and washed with ice water. The ppt was dissolved with a minimal amount of DCM and poured onto a short column of silica gel, and the product (1.2 g, ~ 100 percent) was obtained by column chromatography with DCM. ¹H NMR (400 MHz, CDCl₃) δ 8.42 (s, 1 H), 2.75 (q, 2 H, J = 7.6 Hz), 1.29 (t, 3 H, J = 7.6 Hz).
85.2%	for 3.8 h; Heating / reflux	N, N-DIISOPROPYLETHYLAMINE (195 mL, 0.86 mol) (Aldrich) was added slowly to a mixture of 5-ethyl uracil (52.3 g, 0.37 mol) (from Example LC, suprn) and phosphorous oxychloride (150 mL, 1.61 mol) (Aldrich) with external cooling in a cold water bath. The mixture was heated at reflux for 3.8 hours and cooled to room temperature. Mixture was then poured into ice (300 g). Ethyl acetate (100 mL) was added and mixture stirred at 20 °C for 30 minutes with cooling in an ice-water bath. The resulting mixture was filtered through CELITEE and the filtrate extracted with ethyl acetate-hexanes (1: 1,3 X 300 mL). The combined organic layers was washed with water (250 mL), dried over sodium sulfate, filtered and concentrated to dryness. This residue was dissolved in ethyl acetate- hexanes (1 : 1) and filtered through TLC grade silica gel and eluting with the same solvent. The filtrate was concentrated to dryness to give 2,4-dichloro-5-ethyl-pyrimidine. (Yield 56.3 g, 85.2percent).

Reference： [1] Patent: EP1464335, 2004, A2, . Location in patent: Page/Page column 329
[2] Nucleosides and Nucleotides, 1994, vol. 13, # 1-3, p. 235 - 243
[3] Patent: WO2004/41821, 2004, A1, . Location in patent: Page 26-27
[4] Synthetic Communications, 1992, vol. 22, # 20, p. 2927 - 2934
[5] Collection of Czechoslovak Chemical Communications, 2006, vol. 71, # 4, p. 579 - 594
[6] Journal of Medicinal Chemistry, 2011, vol. 54, # 2, p. 510 - 524

2
[ 63857-18-1 ]
[ 34171-40-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7169 - 7173,5

3
[ 34171-37-4 ]
[ 34171-40-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7169 - 7173,5

[ 34171-40-9 ] Synthesis Path-Downstream 1~84

1
[ 4212-49-1 ]
[ 34171-40-9 ]

Yield	Reaction Conditions	Operation in experiment
~ 100%	With N,N-dimethyl-aniline; trichlorophosphate; at 120℃; for 5h;	Step A: Synthesis of 2,4-dichloro-5-ethylpyrimidine. To a suspension of 5-ethyluracil (1 g, 7.1 mmol) in POCl3 (4.5 mL) was slowly added N,N-dimethylaniline (1 mL). The reaction was heated at reflux (~120 C) for 5 h until the starting material was completely dissolved and the entire solution turned a purple color. The mixture was allowed to cool and poured very slowly into ice (~40 g). The resulting ppt was filtered and washed with ice water. The ppt was dissolved with a minimal amount of DCM and poured onto a short column of silica gel, and the product (1.2 g, ~ 100 %) was obtained by column chromatography with DCM. 1H NMR (400 MHz, CDCl3) delta 8.42 (s, 1 H), 2.75 (q, 2 H, J = 7.6 Hz), 1.29 (t, 3 H, J = 7.6 Hz).
85.2%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; for 3.8h;Heating / reflux;	N, N-DIISOPROPYLETHYLAMINE (195 mL, 0.86 mol) (Aldrich) was added slowly to a mixture of 5-ethyl uracil (52.3 g, 0.37 mol) (from Example LC, suprn) and phosphorous oxychloride (150 mL, 1.61 mol) (Aldrich) with external cooling in a cold water bath. The mixture was heated at reflux for 3.8 hours and cooled to room temperature. Mixture was then poured into ice (300 g). Ethyl acetate (100 mL) was added and mixture stirred at 20 C for 30 minutes with cooling in an ice-water bath. The resulting mixture was filtered through CELITEE and the filtrate extracted with ethyl acetate-hexanes (1: 1,3 X 300 mL). The combined organic layers was washed with water (250 mL), dried over sodium sulfate, filtered and concentrated to dryness. This residue was dissolved in ethyl acetate- hexanes (1 : 1) and filtered through TLC grade silica gel and eluting with the same solvent. The filtrate was concentrated to dryness to give 2,4-dichloro-5-ethyl-pyrimidine. (Yield 56.3 g, 85.2%).

Reference： [1]Patent: EP1464335,2004,A2 .Location in patent: Page/Page column 329
[2]Nucleosides and Nucleotides,1994,vol. 13,p. 235 - 243
[3]Patent: WO2004/41821,2004,A1 .Location in patent: Page 26-27
[4]Synthetic Communications,1992,vol. 22,p. 2927 - 2934
[5]Collection of Czechoslovak Chemical Communications,2006,vol. 71,p. 579 - 594
[6]Journal of Medicinal Chemistry,2011,vol. 54,p. 510 - 524

2
[ 141-52-6 ]
[ 34171-40-9 ]
[ 34171-35-2 ]

Reference： [1]Synthetic Communications,1992,vol. 22,p. 2927 - 2934

3
[ 34171-40-9 ]
[ 111196-81-7 ]

Reference： [1]Nucleosides and Nucleotides,1994,vol. 13,p. 235 - 243

5
[ 156-87-6 ]
[ 34171-40-9 ]
3-(2-chloro-5-ethyl-pyrimidin-4-ylamino)-propan-1-ol [ No CAS ]