[ CAS No. 51-52-5 ] {[proInfo.proName]}

Name: 51-52-5|6-Propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one|97%
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SKU: A115152
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COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 51-52-5 ]

Product Details of [ 51-52-5 ]

CAS No. :	51-52-5	MDL No. :	MFCD00006041
Formula :	C₇H₁₀N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KNAHARQHSZJURB-UHFFFAOYSA-N
M.W :	170.23	Pubchem ID :	657298
Synonyms :	6-n-Propylthiouracil;6-Propyl-2-thiouracil;CTK8G2614;6-(Propyl-d5)-2-thiouracil;Propycil-d5;Propacil-d5;Procasil-d5;Propylthiouracil-d5;NSC 70461;NSC 6498;PTU

Calculated chemistry of [ 51-52-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.43
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.83
TPSA :	80.74 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) :	-6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	0.79
Log Po/w (WLOGP) :	1.39
Log Po/w (MLOGP) :	0.38
Log Po/w (SILICOS-IT) :	3.68
Consensus Log Po/w :	1.57

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.66
Solubility :	3.68 mg/ml ; 0.0216 mol/l
Class :	Very soluble
Log S (Ali) :	-2.07
Solubility :	1.46 mg/ml ; 0.00858 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.86
Solubility :	0.234 mg/ml ; 0.00138 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 51-52-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335-H351-H361	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 51-52-5 ]

* 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 [ 51-52-5 ]
Downstream synthetic route of [ 51-52-5 ]

[ 51-52-5 ] Synthesis Path-Upstream 1~2

1
[ 17356-08-0 ]
[ 30414-54-1 ]
[ 51-52-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In water at 70 - 105℃; for 3 h;	3-Oxohexanoic acid methyl ester (1) (2.95 ml_, 20.81 mmol) and K₂CO₃ (2.819 g, 20,39 mmol) were added to a solution of thiourea (1.044 g, 13.73 mmol) in water (1.8 ml_) at 70⁰C. The obtained mixture was stirred at 105⁰C for 3 hours, cooled to room temperature and diluted with water (7,5 mi_). Thereafter, concentrated aqueous HCI solution (6.75 ml_) was added carefully. The resulting precipitate was collected by filtration, washed with water and dried, giving compound 2 as a white-yellow solid. Yield 1.815 g, 78percent. MW 170.23. LCMS t_R (min): 1.17. MS (APCI+), m/z 171.12 [M-t-hTf.

Reference： [1] Patent: WO2010/118367, 2010, A2, . Location in patent: Page/Page column 51
[2] Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, # 6, p. 1362 - 1368
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7180 - 7184

2
[ 3249-68-1 ]
[ 17356-08-0 ]
[ 51-52-5 ]

Reference： [1] RSC Advances, 2017, vol. 7, # 28, p. 17427 - 17441
[2] Journal of the American Chemical Society, 1945, vol. 67, p. 2197,2200
[3] Bulletin des Societes Chimiques Belges, 1950, vol. 59, p. 689
[4] Zhurnal Obshchei Khimii, 1951, vol. 21, p. 760,762;engl.Ausg.S.837,839
[5] European Journal of Medicinal Chemistry, 1988, vol. 23, # 1, p. 53 - 62
[6] Acta Chemica Scandinavica, 1996, vol. 50, # 5, p. 417 - 421
[7] Medicinal Chemistry Research, 2013, vol. 22, # 10, p. 5036 - 5043

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Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide; In water; at 20 - 40℃; for 4h;	Compound 2 (1.815 g, 10.66 mmol) was dissolved in 1.0 N aqueous NaOH solution (10.8 mL, 10.8 mmol). Then methyl iodide (0.675 mL, 10.80 mL) was added to the obtained solution at room temperature. The reaction mixture was stirred at room temperature for 2 hours, then at 400C for 2 hours and left overnight at room temperature. The resulting precipitate was collected by filtration, washed with water and dried, giving the first portion of compound 3. The mother liquid was treated with acetic acid and the resulting precipitate was washed with water and dried, giving the second portion of compound 3. The two portions were combined. Yield 1.610 g, 82%. MVV 184.26. LCMS tR (min): 1.44. MS (APCI+), m/z 185.10 [M+Hf .
	With sodium hydroxide; In water; at 20℃;	A mixture of 6-n-propyl-2-thiouracil (25.0 g, 0.15 mol), sodium hydroxide (5.9 g, 0.15 mol), iodomethane (10.2 ml, 0.17 mol), and water (300 ml) was stirred at room temperature overnight and then filtered. The resulting solid was dried in vacuo to give the titled compound (25.0 g) as a white solid. The product was used in the subsequent reaction without further purification.
	With sodium hydroxide; In water; at 20℃;	A mixture of 6-n-propyl-2-thiouracil (25.0 g, 0.15 mol), sodium hydroxide (5.9 g, 0.15 mol), iodomethane (10.2 ml, 0.17 mol), and water (300 ml) was stirred at room temperature overnight and then filtered. The resulting solid was dried in vacuo to give the titled compound (25.0 g) as a white solid. The product was used in the subsequent reaction without further purification.

	With sodium hydroxide; In water; at 20℃;	<Step 1> 2-(methylthio)-6-propylpyrimidin-4(3H)-one[330] A mixture of 6-propyl-2-thiouracil (25.0 g, 0.15 mol), sodium hydroxide (5.9 g, 0.15 mol), iodomethane (10.2 ml, 0.17 mol), and water (300 ml) was stirred at room temperature overnight and then filtered. The resulting solid was dried to give the titled compound (25.0 g) as a white solid. The product was used in the subsequent reaction without further purification.
25 g	With sodium hydroxide; In water; at 20℃;	A mixture of 6-n-propyl-2-thiouracil (25.0 g, 0.15 mol), sodium hydroxide (5.9 g, 0.15 mol), iodomethane (10.2 ml, 0.17 mol), and water (300 ml) was stirred at room temperature overnight and then filtered. The resulting solid was dried in vacuo to give the titled compound (25.0 g) as a white solid. The product was used in the subsequent reaction without further purification.

Yield	Reaction Conditions	Operation in experiment
27%	With trichlorophosphate; at 110℃; for 16h;Inert atmosphere;	A stirred solution of 2-thioxo-2,3-dihydropvrirnidin-4 ( iTh-one 96 (1 g, 5.81 mrnol) in phosphoryl trichioride (5 mis) under argon atmosphere was heated to 110 C and stmn?ed for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with ice water (20 mU. neutralized with aqueous saturated NaHCO3 solution (20 mL) and extracted with CK2C 12 (230 rnL). The combined organic extracts were dried over sodium sulfhte, filtered. and concentrated in vacuo to obtain the crude product. The crude product was purified through silica gel column chromatography using 2% EtOAc. hexanes to afford compound 97 ,?JOO rug, 2.7%) as a colorless liquid. TLC: 10% EtOAc/ hexanes (R,: 0.8) II-NMR (CflCI3 400 MHz): 6 7.15 (s, 1Ff), 2.72 (t, J: 7.6 Hz, 211), 1.81-132 (m, 2Ff), 0.99 ii.J 7.6 Hz, 311).
	With trichlorophosphate; for 24h;Heating / reflux;	A solution of <strong>[51-52-5]4-hydroxy-2-mercapto-6-propylpyrimidine</strong> (17.7 g) in phosphorous oxychloride (100 mL) was refluxed for 24 h. The phosphorous oxychloride was evaporated to give an oil which was neutralized with aqueous sodium bicarbonate and extracted with ethyl acetate. Chromatography (2% ethyl acetate in hexanes) provided 7.5 g of 2,4-Dichloro-6-propylpyrimidine.
		Phosphorus oxychloride (100 ml) was slowly added at room temperature to 6-propyl-2-thiouracil (17.7 g, 0.1 mol), which was then stirred at 110C overnight. The reaction mixture was added to ice water and then neutralized with a saturated aqueous solution of sodium bicarbonate. The reaction mixture was extracted with dichloromethane. The organic layer was dried on anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 50/1) to give 10.3 g of the titled compound as pale yellow oil.[631] 1H-NMR (400MHz, CDCl3) delta 7.16(s, 1H), 2.73(t, 2H), 1.78(m, 2H), 0.99(t, 3H)

	With trichlorophosphate; at 110℃;	Phosphorus oxychloride (100 ml) was slowly added to 6-propyl-2-thiouracil (17.7 g, 0.1 mol) at room temperature, which was then stirred at 110C overnight. The reaction mixture was added to an ice water and then neutralized with a saturated aqueous solution of sodium bicarbonate. The reaction mixture was extracted with dichloromethane. The organic layer was dried on anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 50/1) to give 10.3 g of the titled compound as a pale yellow oil.[571] 1H-NMR (400MHz, CDCl3) delta 7.16(s, 1H), 2.73(t, 2H), 1.78(m, 2H), 0.99(t, 3H)
		Preparation 1. 2-chloro-N,N-diethyl-6-propylpyrimidine-4-amine [298] <Step 1> 2,4-dichloro-6-propylpyrimidine[299] Phosphorus oxychloride (100 ml) was slowly added to 6-propyl-2-thiouracil (17.7 g, 0.1 mol), which was then refluxed under stirring at 110C for 24 hours. The reaction mixture was added to an ice water and then neutralized with a saturated aqueous solution of sodium bicarbonate. The reaction mixture was extracted with dichloromethane. The organic layer was dried on anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 50/1) to give 10.3 g of the titled compound as a pale yellow oil.[300] 1H-NMR(400MHz, CDCl3) delta 7.16(s, 1H), 2.73(t, 2H), 1.78(m, 2H), 0.99(t, 3H)
10.3 g	With trichlorophosphate; at 110℃;	Phosphorus oxychloride (100 ml) was slowly added to 6-propyl-2-thiouracil (17.7 g, 0.1 mol) at room temperature, which was then stirred at 110 C. overnight. The reaction mixture was added to an ice water and then neutralized with a saturated aqueous solution of sodium bicarbonate. The reaction mixture was extracted with dichloromethane. The organic layer was dried on anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=50/1) to give 10.3 g of the titled compound as a pale yellow oil. [0512] 1H-NMR (400 MHz, CDCl3) delta 7.16 (s, 1H), 2.73 (t, 2H), 1.78 (m, 2H), 0.99 (t, 3H)

[ CAS No. 51-52-5 ] {[proInfo.proName]}

Quality Control of [ 51-52-5 ]

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Product Details of [ 51-52-5 ]

Calculated chemistry of [ 51-52-5 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 51-52-5 ]

Application In Synthesis of [ 51-52-5 ]

[ 51-52-5 ] Synthesis Path-Upstream 1~2

[ 51-52-5 ] Synthesis Path-Downstream 1~88

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H200	Unstable explosive
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H240	Heating may cause an explosion
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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
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H290	May be corrosive to metals
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H301	Toxic if swallowed
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H303	May be harmful if swallowed