[ CAS No. 14001-63-9 ] {[proInfo.proName]}

Name: 14001-63-9|4-Methyl-2(methylsulfanyl)pyrimidine|97%
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Quality Control of [ 14001-63-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 14001-63-9 ]

CAS No. :	14001-63-9	MDL No. :	MFCD00023242
Formula :	C₆H₈N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UCERVHYBSTYCQS-UHFFFAOYSA-N
M.W :	140.21	Pubchem ID :	821261
Synonyms :

Calculated chemistry of [ 14001-63-9 ]

Physicochemical Properties

Num. heavy atoms :	9
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 :	38.72
TPSA :	51.08 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) :	-6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	1.45
Log Po/w (WLOGP) :	1.51
Log Po/w (MLOGP) :	0.54
Log Po/w (SILICOS-IT) :	1.88
Consensus Log Po/w :	1.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.05
Solubility :	1.25 mg/ml ; 0.00891 mol/l
Class :	Soluble
Log S (Ali) :	-2.13
Solubility :	1.04 mg/ml ; 0.00744 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.51
Solubility :	0.433 mg/ml ; 0.00309 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.35

Safety of [ 14001-63-9 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P403+P233-P405-P501	UN#:	3334
Hazard Statements:	H302-H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 14001-63-9 ]

* 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 [ 14001-63-9 ]
Downstream synthetic route of [ 14001-63-9 ]

[ 14001-63-9 ] Synthesis Path-Upstream 1~6

1
[ 14001-63-9 ]
[ 127-79-7 ]

Reference： [1] Yakugaku Zasshi, 1949, vol. 69, p. 27,29[2] Chem.Abstr., 1950, p. 3453

2
[ 14001-63-9 ]
[ 59215-36-0 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300

3
[ 14001-63-9 ]
[ 135645-65-7 ]
[ 77166-01-9 ]

Reference： [1] Journal of Organic Chemistry, 1991, vol. 56, # 19, p. 5610 - 5614
[2] Journal of Organic Chemistry, 1991, vol. 56, # 19, p. 5610 - 5614

4
[ 14001-63-9 ]
[ 77166-01-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 9, p. 2288 - 2300

5
[ 14001-63-9 ]
[ 1383716-46-8 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 1, p. 72 - 76
[2] Patent: WO2012/85815, 2012, A1,

6
[ 14001-63-9 ]
[ 1383716-33-3 ]

Reference： [1] Patent: WO2012/85815, 2012, A1,

[ 14001-63-9 ] Synthesis Path-Downstream 1~66

1
[ 14001-63-9 ]
[ 15231-48-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Matsukawa; Ohta [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1949, vol. 69, p. 491][Chem.Abstr., 1950, p. 3456] Marshall; Walker [Journal of the Chemical Society, 1951, p. 1004,1015][Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, vol. 24, p. 84]

2
[ 14001-63-9 ]
[ 63170-77-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With hydrazine; In ethanol; for 100h;Heating / reflux;	Based on a reported procedure (VANDERHAEGHE, Claesen, Bull. Soc. CHIM. BELG. 1959, 68, 30). Hydrazine monohydrate (334.7 ML, 6.90 mmol) was added in one portion to a solution of 4-Methyl-2-methylsulfanyl-pyrimidine (357. 9 g, 2.55 mol) in abs. EtOH (890 ML). The resulting mixture was refluxed for 50 h, then hydrazine monohydrate (200 ml) was added and refluxing was continued for 50 h (the reaction was monitored BY 1H NMR). Then it was cooled to 0 C to crystallize and 213 g of crude product was isolated by filtration. Recrystallization from ethanol gave the title compound (184.7 g, 59%) as a white solid. 'H NMR (CDC13, 300 MHz) 8, ppm: 2.40 (S, 3H), 4.00 (broad, 2H), 6.512 (D, 1H, 5 Hz), 7.03 (broad, 1H), 8.24 (d, 1H, 5 Hz).
59%	With hydrazine; In ethanol; for 100h;Heating / reflux;	Based on a reported procedure (Vanderhaeghe, Claesen, Bull. Soc. Chim. Belg. 1959, 68, 30). Hydrazine monohydrate (334.7 ml, 6.90 mmol) was added in one portion to a solution of 4-Methyl-2-methylsulfanyl-pyrimidine (357.9 g, 2.55 mol) in abs. EtOH (890 ml). The resulting mixture was refluxed for 50 h, then hydrazine monohydrate (200 ml) was added and refluxing was continued for 50 h (the reaction was monitored by 1H NMR). Then it was cooled to 0 C. to crystallize and 213 g of crude product was isolated by filtration. Recrystallization from ethanol gave the title compound (184.7 g, 59%) as a white solid. 1H NMR (CDCl3, 300 MHz) delta, ppm: 2.40 (s, 3H), 4.00 (broad, 2H), 6.512 (d, 1H, 5 Hz), 7.03 (broad, 1H), 8.24 (d, 1H, 5 Hz).

Reference： [1]Patent: WO2004/74270,2004,A2 .Location in patent: Page 429
[2]Patent: US2005/176701,2005,A1 .Location in patent: Page/Page column 211
[3]Bulletin des Societes Chimiques Belges,1959,vol. 68,p. 30,55

3
[ 17119-73-2 ]
[ 14001-63-9 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1949,vol. 69,p. 491
Chem.Abstr.,1950,p. 3456

4
[ 14001-63-9 ]
[ 135645-65-7 ]
[ 77166-01-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 5610 - 5614
[2]Journal of Organic Chemistry,1991,vol. 56,p. 5610 - 5614

5
[ 14001-63-9 ]
[ 77166-01-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 2288 - 2300

6
[ 35071-17-1 ]
[ 74-88-4 ]
[ 14001-63-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide; In water; at 20℃;	4-Methylpyrimidine-2-thiol (79.4 g, 488 mmol) was added to 1 M aqueous sodium hydroxide (NaOH) (1.02 L, 1.02 mol). To the stirring mixture was added iodomethane (76.2 g, 540 mmol) and the reaction stirred at room temperature overnight. The mixture was extracted with dichloromethane (3 x 300 mL). The organic phase was dried over magnesium sulfate and concentrated to yield 66.8 g (98%) of 4-methyl-2- (methylsulfanyl) pyrimidine.'H NMR (CDCI3) : 8 8.39 (d, 1 H), 6.84 (d, 1 H), 2.59 (s, 3H), 2.48 (s, 3H) ; MS m/z 141 (M+1).
89.2%	With potassium carbonate; In tetrahydrofuran; at 20℃; for 18h;	Example A-1 : Preparation of reactive intermediates A and B according to Method A Preparation of 4-methyl-2-(methylthio)pyrimidine (2)MeIY K2Co3 gammaSH S^I5 1 2A mixture of compound 4-methylpyrimidine-2-thiol (500 g, 3.05 mol), iodomethane (611 g, 4.27 mol) and K2CO3 (915 g, 6.71 mol) in THF (4 L) was stirred at room temperature for 18 h. The suspension was filtered and the solid was washed with ether (500 mL *2). The filtrate was concentrated and dried in vacuum to give compound 2 (380 g, 89.2%) as a yellow oil.
86%	With sodium hydroxide; In water; at 20℃; for 2h;	To A solution of NAOH (7. 46 G, 186. 4 MMOL) IN WATER (120 ML), 4- METHYLPYRIMIDINE-2-THIOL HYDROCHLORIDE (13. 78 G, 84. 7 MMOL) WAS ADDED AND subsequently iodomethane (13. 23 G, 93. 2 MMOL) WAS ADDED DROPWISE UNDER ARGON atmosphere. It was stirred at room temperature for 2 H. It was extracted with CH2CI2 (X2). The organic phase was dried over NA2S04 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using HEXANE-ETOAC mixtures OF INCREASING POLARITY AS ELUENT, TO AFFORD 10. 26 G OF the desired compound (YIELD : 86%).

	With sodium hydroxide; In ethanol; water; at 20℃; for 16h;	Intermediate 1 4-Methyl-2-(methylthio)pyrimidine A suspension of 2-thio-4-methylpyrimidine (20.0 g) and methyl iodide (7.65 g) in ethanol (615 ml_) and 1 M NaOH (246 ml_) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure to 200 ml_, and then the reaction mixture was extracted with ethyl acetate (300 ml_ x 2). The organic layers were combined and washed with water, brine, and dried with anhydrous Na2SO4. The mixture was filtered and concentrated to afford the title compound as clear brown oil.
		[4-METHYL-2-METHYLSULFANYL-PYRIMIDINE] is prepared from 4-methyl-pyrimidine-2-thiol in analogy to a standard protocol using methyliodide (Strekowski, L.; Wydra, R. L.; Janda, L.; Harden, D. B. J. Org. Chem. (1991), 56 (19), 5610-14). Title compound: single peak at 3.94 min (System 1); Rf = 0.32 (ethyl acetate/hexane 1: 2).

Reference： [1]Patent: WO2003/76441,2003,A1 .Location in patent: Page/Page column 80
[2]Tetrahedron Letters,2009,vol. 50,p. 2552 - 2554
[3]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 40; 57
[4]Patent: WO2004/76450,2004,A1 .Location in patent: Page 39-40
[5]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 347 - 350
[6]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 2288 - 2300
[7]Patent: WO2007/24843,2007,A2 .Location in patent: Page/Page column 31
[8]Patent: WO2004/5282,2004,A1 .Location in patent: Page 48
[9]Journal of Enzyme Inhibition and Medicinal Chemistry,2016,vol. 31,p. 111 - 122

7
[ 14001-63-9 ]
[ 116332-62-8 ]
[ 200801-88-3 ]

Yield	Reaction Conditions	Operation in experiment
		alpha-(2-methylthiopyrimidine-4-yl)-3-trifluromethylacetophenone (3) Under Ar, a solution of diisopropylamine (70 ML, 0.5 mol) in THF (500 ML) was cooled to -70 C. and a solution of 2.5 N n-BuLi in hexane (0.5 mol) was added dropwise.. After addition, the solution was stirred for 0.5 hr at -70 C. and then a solution of 1 (44 g, 0.31 mol) in THF (25 ML) was added dropwise.. After 0.75 hr, a solution of 2 (87.4 g, 0.38 mol) in THF (25 ML) was added dropwise.. The reaction was stirred at -70 C. for an additional 2 hr and then treated with a saturated solution of aqueous NaHCO3.. The aqueous layer was extracted with EtOAc (3*) and the combined organic extract was washed with brine, dried, filtered and concentrated to dryness to yield a solid.. The solid was crystallized from methylene chloride-hexanes to yield 66g of impure product which was further triturated with 30% ether-hexanes to yield 45g of 3.. Further chromatography of the mother liquors on a Still column (100 mm) and elution with 15% ethyl acetate-hexanes yielded another 32.6g to yield a total of 77.6g of 3.
		In a 500 mL round-bottom flask equipped with a stir bar, under N2, was charged compound 1 (10.45 g, 74.53 mmol) and THE (300 mL). The flask was cooled in an acetone dry ice bath 0.5 h, then 1. 5 M LDA IN THF (80 ML, 120 mmol) was slowly added. The resulting mixture was stirred 0.75 h, then 6 (20.59 g, 88. 30 mmol) was added in THF (40 mL), followed by stirring 2 h. Saturated sodium bicarbonate (100 ML) was added and after stirring 10 min, the volume of THE was reduced by rotary evaporation. The crude was dissolved in EtOAc (400 ML) and washed by saturated sodium bicarbonate followed by brine. The resulting organic layer was collected, dried over NA2S04 and concentrated in vacuum. Purification by flash chromatography, (SiO2, 20% EtOAc/hexanes) gave the compound 7 as a yellow solid. MS (ES+): 313 (M+H) +.
		Step 1-B 2-(2-Methylthiopyrimidin-4-yl)-1-(3-trifluoromethylphenyl)ethanone To a solution of diisopropylamine (7.9 mL, 0.056 mole) in THF (100 mL) at -78C under argon was added 2.5M N-butyllithium (22.5 mL, 0.056 mole), followed after 5 minutes by a solution of <strong>[14001-63-9]2-methylthio-4-methylpyrimidine</strong> (5.27 g, 0.0376 mole) in THF (20 mL). Upon stirring for 15 min. at -78C, a solution of N-methoxy-N-methyl-3-trifluoromethylbenzamide (9.63 g, 0.041 mole) in THF (90 mL) was added. The reaction was allowed to warm to 0C and then quenched by pouring into water (400 mL) and ethyl acetate (400 mL). The layers were separated and the aqueous layer washed with ethyl acetate (200 mL). The ethyl acetate extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a solid (11.9 g). Trituration with 10% ether/hexane (100 mL) gave 9.5 g of the title compound. 1H NMR (CDCl3) (mixture of keto-and enol tautomers) d 6.0-8.5 (m, 6H, rotamers), 2.4-2.7 (m, 3H),.

Reference： [1]Patent: WO2006/21449,2006,A1 .Location in patent: Page/Page column 7
[2]Journal of Medicinal Chemistry,1999,vol. 42,p. 2180 - 2190
[3]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2409 - 2413
[4]Patent: US6350744,2002,B1 .Location in patent: Page column 13
[5]Patent: WO2004/94379,2004,A2 .Location in patent: Page 24-25
[6]Patent: EP906307,2005,B1 .Location in patent: Page/Page column 27

8
[ 14001-63-9 ]
sodium-compound of/the/ sulfanilamide [ No CAS ]
[ 127-79-7 ]

Reference： [1]Patent: US2471772,1945,

9
[ 14001-63-9 ]
[ 451-46-7 ]
[ 217661-99-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hexamethyldisilazane; In tetrahydrofuran; at 20℃; for 2h;	To A solution of 4-methyl-2-(methylsulfanyl)pyrimidine (21.00 g, 150.0 mmol, obtained in reference example 6, section A) and ethyl 4-fluorobenzoate (25. 14 G, 150. 0 MMOL) IN THF (300 ML) UNDER ARGON ATMOSPHERE, A SOLUTION OF SODIUM BIS (TRIMETHYLSILYL) AMIDE (150 ML OF A 2 M SOLUTION IN THF, 300 MMOL) IN THF (150 ML) was added dropwise while cooling with an ice-bath. It was stirred at room temperature for 2 H. Saturated NH4Cl was added and the solvent was evaporated. The residue was taken up in A mixture of ETOAC and water and the phases were separated. The aqueous phase was REEXTRACTED with ETOAC. The combined organic PHASES WERE WASHED WITH BRINE, DRIED OVER NA2S04 AND CONCENTRATED TO dryness, to afford 36. 36 g of the title compound (yield: 93%). H NMR (300 MHz, CDCI3) 8 (TMS) : 2. 52 (KETONE : S, 3 H), 2. 61 (ENOL : S, 3 H), 4. 35 (KETONE : S, 2 H), 5.92 (enol: s, 1 H), 6.64 (enol: d, J = 5.7 Hz, 1 H), 6. 95 (KETONE : D, J = 5. 1 HZ, 1 H), 7. 08-7. 19 (M, 2H), 7. 83 (ENOL : M, 2 H), 8. 07 (KETONE M, 2 H), 8. 31 (ENOL : D, J = 5. 7 HZ, 1 H), 8. 56 (KETONE : D, J = 5. 1 HZ, 1 H).
93%		b) 1-(4-FIuoro-phenyI)-2-(2-methylsuIfanyl-pyrimidin-4-yI)-ethanone; To a solution of 4-methyl-2-(methylsulfanyl)pyrimidine (21.00 g, 150.0 mmol) andethyl 4-fluorobenzoate (25.14 g, 150.0 mmol) in THF (300 ml) under argonatmosphere, a solution of sodium hexamethyldisilazide (150 ml of a 2 M solutionin THF, 300 mmo.) in THF (150 ml) was added dropwise while cooling with an ice-bath. It was stirred at room temperature for 2 h. Saturated NH4CI solution was added and the solvent was evaporated. The residue was taken up in a mixture of EtOAc and water and the phases were separated. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SC>4 and concentrated to dryness, to afford 36.36 g of the title compound (yield: 93%).
85%	With lithium hexamethyldisilazane; In tetrahydrofuran; at 23 - 45℃; for 15h;	Intermediate 1: 2-(4-Fluorophenyl)-7-(methylthio)pyrazolo[1,5-c]pyrimidine. Step A: 1-(4-Fluorophenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethanone. A solution 4-methyl- 2-(methylthio)pyrimidine (3.0 mL, 2.01 mmol) and ethyl 4-fluorobenzoate (6.1 mL, 42.0 mmol) in THF (60 mL) at 23 C was treated with 1.0 M solution of LHMDS in THF (42 mL, 42.0 mmol). The reaction warmed to 45 C for 15 h. The mixture was diluted with water and extracted with EtOAc. The combined organics were dried (MgSO4), filtered, concentrated under reduced pressure. Purification (SiO2, EtOAc / heptane gradient 0 to 10%) afforded the title compound (5.6 g, 85%).

14%		Synthesis of 1-fluoro-4-[4-(2-methylthiopyrimidinyl)acetyl]benzene Into 100 mL of a THF solution containing 12.64 g of 4-methyl-2-thiopyrimidine, 54.1 mL of 2M LDA heptane, THF, ethylbenzene solution was dropped at -78C, and thereafter stirred for 15 minutes at -78C. Then 100 mL of a THF solution containing 15.17 g of ethyl-4-fluorobenzoate was dropped thereinto at -78C. After the end of the dropping, the solution was stirred for an hour while slowly raising the temperature to room temperature. Fifty(50) mL of saturated aqueous ammonium chloride solution and 50 mL of water were added to the reaction solution, followed by extraction with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate and removed of the solvent by distillation under reduced pressure. The residue was dissolved in chloroform and purified on 120 g silica gel column chromatography (eluent, hexane: ethyl acetate = 4:1). Washing the purified residue with hexane, 3.39 g (yield: 14%) of the title compound was obtained as a pale yellow crystal. 1H-NMR(CDCl3)delta: 14.61(s, 1H), 8.30(d, J=5.4Hz, 1H), 7.83(dd, J=5.3Hz, 8.9Hz, 2H), 7.10(t, J=8.9Hz, 2H), 6.63(d, J=5.4Hz, 1H), 5.90(s, 1H), 2.61(s, 3H).
	With ammonium chloride; lithium; In tetrahydrofuran;	Reference Example 9 1-(4-fluorophenyl)-2-(2-methylsulphanylpyrimidin-4-yl)-1-ethanone A solution of lithium hexamethyidisilazane in tetrahydrofuran (1.221, 1M), at -40 C., was treated with a solution of 4-methyl-2-methylsulphanylpyrimidine (76.03 g) in tetrahydrofuran (100 ml). The solution was warmed to 0 C., then stirred for 15 minutes, then cooled to -40 C., then treated with a solution of ethyl 4-fluorobenzoate (91.32 g) in tetrahydrofuran (200 ml). After stirring at -40 C. for 15 minutes the reaction mixture was allowed to warm to room temperature over 2 hours, then treated with ammonium chloride solution. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were evaporated to give the title compound (136.19 g), m.p. 212-214 C. MH+ 263.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 693 - 696
[2]Patent: WO2004/76450,2004,A1 .Location in patent: Page 45-46
[3]Patent: WO2006/13095,2006,A2 .Location in patent: Page/Page column 44-45
[4]Patent: WO2016/176457,2016,A1 .Location in patent: Page/Page column 85
[5]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 267 - 272
[6]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5689 - 5692
[7]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3168 - 3173
[8]Patent: EP1832584,2007,A1 .Location in patent: Page/Page column 67
[9]Patent: US6602877,2003,B1

10
[ 4637-24-5 ]
[ 35071-17-1 ]
[ 14001-63-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In toluene; for 6.5h;Heating / reflux;	Example 310; 3-(4-Fluorophenyl)-4-[4-(2-methylthio)pyrimidinyl]-5-(phenylacetylamino)isoxazole; a: Synthesis of 4-methyl-2-methylthiopyrimidine; To 400 mL of a toluene solution containing 25.5 g of 2-(4-methylpyrimidine)thiol, 50 mL of DMFDMA and then 42 mL of diisopropylethylamine were added and heated under reflux for 6.5 hours. The reaction solution was cooled, removed of the solvent by distillation under reduced pressure, and the residue was extracted with chloroform after addition of water. The chloroform extract was dried over anhydrous magnesium sulfate and removed of the solvent by distillation under reduced pressure. The residue was purified on 120 g silica gel column chromatography (eluent, chloroform) to provide 24.13 g (yield: 85%) of the title compound as a brown oily substance. 1H-NMR(CDCl3)delta: 8.36(d, J=5.1Hz, 1H), 6.80(d, J=5.1Hz, 1H), 2.56(s, 3H), 2.45(s, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 693 - 696
[2]Patent: EP1832584,2007,A1 .Location in patent: Page/Page column 67

11
[ 14001-63-9 ]
[ 403-33-8 ]
[ 217661-99-9 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 2173 - 2184
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4006 - 4010
[3]European Journal of Medicinal Chemistry,2007,vol. 42,p. 1334 - 1357
[4]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2479 - 2483
[5]Journal of Medicinal Chemistry,2010,vol. 53,p. 7938 - 7957

12
[ 14001-63-9 ]
[ 13331-27-6 ]
2-(3-nitrophenyl)-4-methylpyrimidine [ No CAS ]

Reference： [1]Organic letters,2002,vol. 4,p. 979 - 981

13
[ 14001-63-9 ]
[ 94839-07-3 ]
2-(3,4-methylenedioxyphenyl)-4-methylpyrimidine [ No CAS ]

Reference： [1]Organic letters,2002,vol. 4,p. 979 - 981

14
[ 6959-66-6 ]
[ 74-88-4 ]
[ 14001-63-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydroxide; In water; at 20℃; for 2h;	REFERENCE EXAMPLE 5; 1-(4-Fluoro-phenyl)-2-(2-methylsulfanyl-pyrimidin-4-yl)-propenone ;a); 4-Wlethyl-2-(methyisuIfanyl)pyrimidine;To a solution of NaOH (7.46 g, 186.4 mmol) in water (120 ml) was added 4-methylpyrimidine-2-thiol hydrochloride (13.78 g, 84.7 mmol) and subsequently iodomethane (13.23 g, 93.2 mmol) was added dropwise under argon atmosphere. It was stirred at room temperature for 2 h and then extracted with CH2Cl2 (2x). The organic phase was dried over NaaSCU and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 10.26 g of the desired compound (yield: 86%).
81%		In a 5L three-necked round-bottomed flask equipped with an overhead stirrer and reflux condenser, 497.6 g (3.06 mol) of the hydrochloride salt of the thiol pyrimidine 1 was suspended in 1L of MeOH. A 6N [NAOH] solution (1.2 L, excess) was added and the mixture was stirred for 15 minutes. The solution was heated to reflux and methyl iodide (192 mL, 3.08 mol) was added in portions. The mixture was refluxed for two hours, cooled, and extracted with [CH2CL2.] The extract was dried [(MGS04)] and evaporated in vacuo to afford 347.3 g [(81%)] of the sulfide as a light yellow oil.
	With sodium hydroxide; In water; at 20℃;	Based on a reported procedure (Ishizumi, K.; Kojima, A. ; Antoku, F. Chem PLAARM Bull 1991,39, 2288). Sodium hydroxide (92.5 g, 2.31 mol) was added to a suspension of 2-mercapto-4-methyl pyrimidine hydrochloride (150 g, 0.93 mol) in water (1.5 L). Methyl iodide (78.9 ml, 1.39 mol) was rapidly added to the clear solution (solution temp. < 20 C). After overnight stirring, diethyl ether (400 mL), the organic layer was separated and the aqueous layer was extracted with diethyl ether (4X200 ML) all organic layers were combined, washed with 5% aq. NAOH solution (100 ML), brine (200 ML, 2 times), and dried (MGS04), concentrated in vacuo to afford 119.3 g of crude material (95% pure by NMR) which was used in the next step without purification. 'H NMR (CDC13, 300 MHz) 8, ppm: 2.46 (s, 3H), 2.56 (S, 3H), 6.82 (d, J=5 Hz, 1H, ), 8.37 (d, J=5 Hz 1H).

	With sodium hydroxide; In water; at 20℃;	Based on a reported procedure (Ishizumi, K.; Kojima, A.; Antoku, F. Chem Pharm Bull 1991, 39, 2288). Sodium hydroxide (92.5 g, 2.31 mol) was added to a suspension of 2-mercapto-4-methyl pyrimidine hydrochloride (150 g, 0.93 mol) in water (1.5 L). Methyl iodide (78.9 ml, 1.39 mol) was rapidly added to the clear solution (solution temp. <20 C.). After overnight stirring, diethyl ether (400 mL), the organic layer was separated and the aqueous layer was extracted with diethyl ether (4×200 ml) all organic layers were combined, washed with 5% aq. NaOH solution (100 ml), brine (200 ml, 2 times), and dried (MgSO4), concentrated in vacuo to afford 119.3 g of crude material (95% pure by NMR) which was used in the next step without purification. 1H NMR (CDCl3, 300 MHz) 6, ppm: 2.46 (s, 3H), 2.56 (s, 3H), 6.82 (d, J=5 Hz, 1H,), 8.37 (d, J=5 Hz 1H).
	With sodium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃;	In a 500 ML round-bottom flask equipped with a stir bar, under N2, was charged 4- METHYLPYRIMIDINE-2-THIOL hydrochloride (31.92 g, 196. 3 mmol), sodium carbonate (63.28 g, 597.0 mmol) and DMF (300 mL). To the resulting solution was added iodomethane (25.0 ML, 401.6 mmol) and the reaction was stirred at room temperature overnight. The resulting mixture was concentrated onto SI02 and eluted with 20% ETOAC/HEXANES to give compound 1 as a YELLOW/BROWN oil. MS (ES+): 141 (M+H) +.

Reference： [1]Journal of Chemistry,2015,vol. 2015
[2]Organic letters,2002,vol. 4,p. 979 - 981
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4006 - 4010
[4]Journal of Medicinal Chemistry,2002,vol. 45,p. 2173 - 2184
[5]Patent: WO2006/13095,2006,A2 .Location in patent: Page/Page column 44
[6]Patent: WO2004/22555,2004,A1 .Location in patent: Page 9-10; 18
[7]Patent: WO2004/74270,2004,A2 .Location in patent: Page 428-429
[8]Patent: US2005/176701,2005,A1 .Location in patent: Page/Page column 210
[9]Patent: WO2004/94379,2004,A2 .Location in patent: Page 21-22

15
[ 6959-66-6 ]
[ 4637-24-5 ]
[ 14001-63-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In toluene; for 4h;Heating / reflux;	Step 1-A 2-Methylthio-4-methylpyrimidine To 2-mercapto-4-methylpyrimidine·HCl (50.0g, 0.307mole) in toluene (750 mL), under argon, was added diisopropylethylamine (80.0 mL, 0.461 mole) followed by N,N-dimethylformamide dimethyl acetal (100 mL) and the mixture heated to reflux for 4 hours. Upon cooling, the reaction was concentrated in vacuo to an oil, dissolved in ether (400 mL), and washed with water (2x50 mL). The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to an oil which was vacuum distilled to give 2-methylthio-4-methylpyrimidine (36.4 g) as an oil. 1H NMR(CDCl3) d 8.37 (d, 1H, J = 7.5Hz), 6.82 (d, 1H, J = 7.5Hz), 2.55 (s 3H), 2.45 (s, 3H).

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 1334 - 1357
[2]Patent: WO2006/21449,2006,A1 .Location in patent: Page/Page column 7
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2479 - 2483
[4]Patent: EP906307,2005,B1 .Location in patent: Page/Page column 27

16
[ 7234-25-5 ]
[ 14001-63-9 ]

Reference： [1]Il Farmaco,1993,vol. 48,p. 335 - 355

17
[ 14001-63-9 ]
[ 127-79-7 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1949,vol. 69,p. 27,29
Chem.Abstr.,1950,p. 3453

18
[ 14001-63-9 ]
[ 95-92-1 ]
C₁₀H₁₂N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium tert-butylate; In tetrahydrofuran;	In a 5L three-necked round-bottomed flask equipped with an overhead stirrer, 4-methyl-2-thiomethylpyrimdine (344.5 g, 2.46 mol) was dissolved in 2L of THF. Diethyl oxalate (334 [ML,] 2.46 mol) was added. Potassium t-butoxide (286.22 g, 2.55 mol) was added in 50 g portions. Each portion produced a mild exotherm. The mixture rapidly turned brown and a yellow precipitate eventually formed forming a thick mixture. The reaction was poured into 10% aqueous [NH4CL] and extracted with [CH2CL2.] The extract was dried [(MGS04)] and filtered through a plug of silica gel. The plug was eluted with [10%] [ETOAC/CH2CL2.] The filtrate was evaporated to afford a brown solid. The solid was dissolved in a minimal amount of [CH2C12.] Hexane was added and the solution was cooled to precipitate a solid that was filtered. The filtrate was evaporated and the precipitation process was repeated to afford a total of 401.5 g (60%) of the ketoester 3.

Reference： [1]Patent: WO2004/22555,2004,A1 .Location in patent: Page 9-10; 18

19
[ 14001-63-9 ]
[ 451-46-7 ]
1-(4-fluorophenyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]ethanone [ No CAS ]
[ 217661-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20℃; for 1.66667h;	To a O C solution of 4-methyl-2- (methylsulfanyl) pyrimidine (66.8 g, 477 mmol) and ethyl 4- fluorobenzoate (80.2 g, 477 mmol) in tetrahydrofuran (390 mL) was added a solution of 1 M lithium bis (trimethylsilyl) amide (954 mL, 954 mmol) in tetrahydrofuran (THF) dropwise via an addition funnel. The reaction was stirred for 10 minutes and allowed to warm to room temperature. The reaction was stirred at room temperature for 1.5 hours and then carefully quenched with water. The mixture was extracted with ethyl acetate (3 x 300 mL) before the organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized from dichloromethane and hexanes to yield 91.4 g (75%) of 1- (4-fluorophenyl)-2- [2- (methylsulfanyl) pyrimidin- 4-yl] ethanone as a mixture of tautomers. Tautomer A :'H NMR (CDC13) : 8 8.50 (d, 1 H), 8.12 (dd, 2H), 7.18 (m, 2H), 7.02 (d, 1 H), 4.39 (s, 2H), 2.56 (s, 3H). MS m/z 263 (M+1). Tautomer B :'H NMR (CDCI3) : 8 8.35 (d, 1 H), 7.87 (dd, 2H), 7.16 (m, 3H), 6.68 (d, 1 H), 5.96 (s, 1 H), 2.65 (s, 3H). MS mlz 263 (M+1).

Reference： [1]Patent: WO2003/76441,2003,A1 .Location in patent: Page/Page column 80-81

20
[ 14001-63-9 ]
[ 614-99-3 ]
[ 868360-43-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at 20℃;	Lithium bis (trimethylsilyl)amide M in hexanes, 100 mL, 100 mmol) was added dropwise over 60 minutes to a solution of 4-methyl-2- (methylthio)pyrimidine g, 50.0 mmol) and ethyl 2-furoate (7.70 g, 55.0 mmol) in tetrahydrofuran (22 mL) under an atmosphere of nitrogen. The mixture was stirred at ambient temperature overnight then hexane (200 mL) was added and the precipitate was filtered. The solid was treated with saturated aqueous ammonium chloride solution, filtered and washed with water and dried. Purification by flash chromatography (8: 2 ethyl acetate/hexanes to 5: 1 ethyl acetate/hexanes) gave the title compound (10.32 g, 88%) as a yellow solid. # 1H NMR (DMSO) showed a mixture of enol and keto tautomers: Keto tautomer: 2.42 (s, 3H), 4.35 (s, 2H), 6.75 (dd, 1 H), 7.22 (d, 1 H), 7.60 (dd, 1 H), 8.05 (d, 1 H), 8.60 (d, 1 H). Enol tautomer: 2.42 (s, 3H), 6.18 (s, 1 H), 6.70 (dd, 1 H), 7.05 (m, 2H), 7.90 (d, 1 H), 8.45 (d, 1H). ESI/MS (m/e, %) : 235 [(M+1) +, 100].

Reference： [1]Patent: WO2005/100353,2005,A1 .Location in patent: Page/Page column 32

21
[ 14001-63-9 ]
[ 116332-54-8 ]
[ 217661-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - 20℃;	Under an atmosphere of nitrogen at -78 C., n-BuLi (1.6 M in hexanes, 8.4 mL) is added dropwise to a solution of diisopropylamine (2.9 mL) in anhydrous tetrahyrofuran (40 mL). After stirring for 5 min, a solution of 4-methyl-2-(methylthio)pyrimidine (2.0 g) in anhydrous tetrahydrofuran (20 mL) is added and stirring continued for a further 30 min at -78 C., whereupon a solution <strong>[116332-54-8]4-fluoro-N-methoxy-N-methylbenzamide</strong> (2.8 g) in anhydrous tetrahyrofuran (20 mL) is added. The solution is allowed to warm to room temperature and then poured into a mixture of ethyl acetate and water. The layers are separated, the aqueous extracted with ethyl acetate and the combined organic phases dried over sodium sulfate. Filtration and evaporation of the solvent followed by tituration of the residue with a mixture of diethyl ether and hexanes (1:10) furnishes the title compound, 73 (3.1 g). The compound obtained in this step shows the following mass spectral data: LC/MS: C13H11FN2OS requires 262.1; observed M/Z 263.2 [M+H]+. RT 4.81 min

Reference： [1]Patent: US2005/261354,2005,A1 .Location in patent: Page/Page column 96; 97

22
[ 14001-63-9 ]
[ 116332-54-8 ]
4-Fluoro-2-(2-methylthio-4-pyrimidinyl)acetophenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.5 g (65%)	With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;	a 4-Fluoro-2-(2-methylthio-4-pyrimidyl)acetophenone nBuLi (10 ml of a 1.6 M solution in hexane; 12 mmol) is added at -78 C. to a solution of diisopropylamine (2.48 ml; 17 mmol) in THF (15 ml) and stirred for 5 min. 4-Methyl-2-(methylthio)pyrimidine (2 g; 14.5 mmol) dissolved in THF (2 ml) is added dropwise and stirred for 30 mm at -78 C. 4-Fluoro-N-methoxy-N-methylbenzamide (2.66 g; 14.5 mmol) is dissolved in THF (3 ml) and added slowly to the reaction mixture. The mixture is warmed to r.t. within 45 min. and poured on water and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4 and evaporated to dryness to yield 2.5 g (65%) of yellow crystals after recrystallisation from tert.butyl methyl ether/hexane. 1H-NMR (200 MHz CDCl3): 3.00 (s, 3H): 6.30 (s, 1H); vinyl-H of enol); 7.00 (d, 1); 7.50 (dd, 2H); 8.20 (dd, 2H); 8.7 (d, 2H). Due to pH-dependent keto-enol tautomerism, signals may be duplicated.
2.5 g (65%)	With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;	b 4-Fluoro-2-(2-methylthio-4-pyrimidinyl)acetophenone n-BuLi (10 ml of a 1.6 M solution in hexane; 12 mmol) is added at -78 C. to a solution of diisopropylamine (2.48 ml; 17 mmol) in THF (15 ml) and stirred for 5 min. 4-Methyl-2-(methylthio)pyrimidine (2 g; 14.5 mmol) dissolved in THF (2 ml) is added dropwise and stirred for 30 min at -78 C. 4-Fluoro-N-methoxy-N-methylbenzamide (2.66 g; 14.5 mmol) is dissolved in THF (3 ml) and added slowly to the reaction mixture. The mixture is warmed to r.t. within 45 min. and poured on water and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4 and evaporated to dryness to yield 2.5 g (65%) of yellow crystals after recrystallisation from tert.butyl methyl ether/hexane. 1H-NMR (200 MHz CDCl3): 3.00 (s, 3H); 6.30 (s, 1H; vinyl-H of enol); 7.00 (d, 1H); 7.50 (dd, 2H); 8.20 (dd, 2H); 8.7 (d, 2H). Due to pH-dependent keto-enol tautomery, signals may be duplicated.

Reference： [1]Patent: US2002/49220,2002,A1
[2]Patent: US6608072,2003,B1

23
[ 156-81-0 ]
[ 6959-66-6 ]
[ 14001-63-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water; ethyl acetate;	EXAMPLE 3 Imidazo[1,2-a]pyrimidin-7-amine, 2-Phenyl-3-(4-pyridinyl) A solution of 1.2 g (11 mmoles) of <strong>[156-81-0]2,4-diaminopyrimidine</strong> in 10 ml of ethanol was heated to 80 C. A solution of 1.0 g (2.8 mmol) of the bromide in 20 ml of ethanol was added drop-wise by addition funnel. The reaction was stirred at 80 C. for 3 hours then cooled to room temperature. Approximately one-half of the solvent was removed in vacuo. Upon cooling to room temperature the reaction was filtered. The filtrate was concentrated in vacuo, diluted with 250 ml ethyl acetate and washed with 2100 ml 0.5M sodium hydroxide solution, dried over sodium sulfate, filtered, and concentrated in vacuo to give a red-brown oil. Trituration of the residue with EtOAc, followed by filtration gave 0.108 g of Compound 5 as an off-white solid. MH+=288. 13.23 g (93.2 mmoles) of lodomethane was added drop-wise by syringe to a solution of 13.38 g (84.73 mmoles) of 2-mercapto-4-methylpyrimidine hydrochloride and 7.46 g (186.4 mmoles) sodium hydroxide in 120 ml of water. After 2 hours the reaction was extracted with 2125 ml dichloromethane. The organic layers were separated, combined, dried over Na2SO4, filtered, and concentrated in vacuo to give 11.14 g (79.45 mmoles) of 4-methyl-2-(methylthio)pyrimidine as a red oil. MH+=140.9.

Reference： [1]Patent: US6610697,2003,B1

24
[ 14001-63-9 ]
[ 736-40-3 ]
N-(4-{2-[2-methylthio-pyrimidin-4-yl]acetyl}phenyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0℃; for 3h;	Intermediate 3 N-(4-(2-r2-(Methylthio)-4-pyrimidinvnacetyl\|phenv?benzamide A suspension of 4-methyl-2-(methylthio)pyrimidine (3.5 g) and ethyl 4- [(phenylcarbonyl)aminojbenzoate (6.72 g) in THF (160 mL) was treated with 1 M EPO <DP n="33"/>lithium Dis(jriotameiny?siotayiota;amiotaalphae solution in THF (80 ml_) at -78 C. The reaction mixture was warmed to 0 0C over the period of 3h. The reaction mixture was then poured into a 1 :1 mixture of 1 M hydrochloric acid/ice (80 ml_ each) and stirred for 2h. The reaction mixture was filtered to afford the title compound as a yellow solid. ESI MS {m/z) 364 [M+H]+; LC-MS, fa (enol) = 2.10 min, fa (ketone) = 2.52 min.

Reference： [1]Patent: WO2007/24843,2007,A2 .Location in patent: Page/Page column 31-32

25
[ 14001-63-9 ]
[ 950525-98-1 ]
[ 950525-75-4 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation b-12-e; phiO-fS-chloro-delta-^rityloxy^phenvn-IH-pyrazol-phivD^-dinethylthio^pyrimidine; To a mixture of 4-methyl-2-(methylthio)pyrimidine (1.4 g, 10 mmol) and methyl 3-chloro-5- (trityloxy)benzoate (4.3 g, 10 mmol) in tetrahydrofuran (50 ml_) was added a 1.0 M tetrahydrofuran solution of LiHMDS (20.0 mL, 20.0 mmol). The mixture was stirred at room temperature for 4 hours then a 4 molar dioxane solution of hydrochloric acid was added (50 mL). The mixture was diluted with ethyl acetate (100 mL) and water (100 mL) then the layers were separated. The aqueous layer was extracted with ethyl acetate (2 X 50 mL). Combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to furnish 5.3 grams of a solid, which was used in the next step without any purification. A mixture of 1-[3-chloro-5-(trityloxy)phenyl]-2-[2-(methylthio)pyrimidin-4-yl]ethanone (5.3 g, 10 mmol) and (dimethoxymethyl)dimethylamine 1,1-dimethoxy-lambda/,lambda/-dimethylmethanamine (3.6 g, 30 mmol) in toluene (100 mL) was stirred at reflux for 2 hours then concentrated to dryness. The residue was dissolved in ethanol (60 mL) then treated with hydrazine (3.20 g, 100 mmol). The mixture was stirred at room temperature for 2 hours. The resulting precipitate was filtered, washed with ethanol, and dried under vacuum to give the title compound as a solid (4.57 g, 82%). 1H NMR (400 MHz, DMSO-D6) delta 2.21 (s, 3 H), 6.56 - 6.67 (m, 1 H), 6.85 - 6.95 (m, 1 H), 6.98 - 7.10 (m, 2 H), 7.20 - 7.50 (m, 15 H), 8.34 (s, 1 H), 8.43 (d, J = 5.3 Hz, 1 H), 12.7 - 13.8 (broad, 1 H).

Reference： [1]Patent: WO2007/105058,2007,A2 .Location in patent: Page/Page column 54

26
[ 14001-63-9 ]
[ 950526-01-9 ]
[ 1241896-12-7 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation b-6-c; 4-(3-(3-methyl-5-(trityloxy)phenyl)-1 H-pyrazol-4-yl)-2-(methvlthio)pvrimidine; To a solution of methyl 3-methyl-5-(trityloxy)benzoate (10.0 g, 24.5 mmol) and 4-methyl-2- (methylthio)pyrimidine (3.77 g, 26.9 mmol) in tetrahydrofuran (40 mL) was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (36.8 mL, 36.8 mmol) at 0 0C under nitrogen. The mixture was warmed to ambient temperature and stirred for 18 hours. Saturated aqueous ammonium chloride was introduced and the mixture extracted with ethyl acetate (3 x 150 mL). The combined organics were washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate), filtered and concentrated to provide 1-(3-methyl-5-(trityloxy)phenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethanone as a mixture of keto / enol tautomers. To a solution of 1-(3-methyl-5-(trityloxy)phenyl)-2-(2- (methylthio)pyrimidin-4-yl)ethanone (12.6 g, 24.5 mmol) in toluene (42 mL) was added N1N- dimethylformamide dimethyl acetal (33 mL, 245 mmol). The mixture was then heated at 90 0C overnight and allowed to cool to ambient temperature. The solution was concentrated to provide crude 3- (dimethylamino)-1-(3-methyl-5-(trityloxy)phenyl)-2-(2-(methylthio)pyrimidin-4-yl)prop-2-en-1-one. To 3- <n="47"/>(dimethylamino)-1-(3-methyl-5-(trityloxy)phenyl)-2-(2-(methylthio)pyrimidin-4-yl)prop-2-en-1-one in absolute ethanol (122 mL) was added hydrazine monohydrate (2.4 mL, 49 mmol). The mixture was stirred at ambient temperature for 1 hour. The precipate that formed was filtered and the resulting solid was dried in vacuo to give the title compound (10.3 g, 81% after 3 steps). 1H NMR (400 MHz, DMSO-D6) delta ppm 2.08 (s, 3 H), 2.27 (s, 3 H), 6.54 (s, 1 H), 6.56 (s, 1 H), 6.73 - 6.80 (m, 2 H), 7.13 - 7.50 (m, 16 H), 8.32 (d, J=5.29 Hz, 1 H).

Reference： [1]Patent: WO2007/105058,2007,A2 .Location in patent: Page/Page column 45-46

27
[ 14001-63-9 ]
[ 180636-50-4 ]
[ 1001922-31-1 ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 1334 - 1357

28
[ 14001-63-9 ]
[ 1126-46-1 ]
[ 616196-42-0 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 2552 - 2554
[2]European Journal of Medicinal Chemistry,2007,vol. 42,p. 1334 - 1357

29
[ 14001-63-9 ]
[ 106614-28-2 ]
[ 1001922-34-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 1334 - 1357

30
[ 14001-63-9 ]
[ 82702-31-6 ]
[ 1001922-29-7 ]

Reference： [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 1334 - 1357

31
[ 14001-63-9 ]
[ 78191-00-1 ]
1-[2-(methylsulfanyl)pyrimidin-4-yl]propan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4-Methyl-2-methylsulfanyl-pyrimidine (14 g; 94.9 mMol) is dissolvedin THF anhydrous under argon andcolled to -78C. Within 60 min. LDA (2 M soln in hexane; 71 mL; 140 mMol) is added dropwise while keeping the temperature < -75C. Stirring is continued for 3 h followed by addition of N-methoxy-N-methylacetamide (10.0 g; 94.9 mMol) at -75C. After this, cooling is removed and the mixture is allowed to stir at RT for 3 h. After removal of the solvent under reduced pressure, the residue is taken up into CH2CI2 (250 mL), washed with water (100 mL) and brine (100 mL). The combined organics are dried over Na2SO4, filtered off and freed from the solvent under reduced pressure. Purification is done by chromatography on silica gel (Redisep 40 g; hexane /EtOAc 3/1 ) to obtain the title compound (4.29 g) as yellow oil. Title compound: MS(ESI+):m/z= 183.1 (M+H)+; HPLC: tRet = 3.714 minutes .

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 210 - 214
[2]Patent: WO2008/138834,2008,A1 .Location in patent: Page/Page column 136

32
[ 14001-63-9 ]
[ 207681-67-2 ]
[ 616196-33-9 ]

Yield	Reaction Conditions	Operation in experiment
77%		Example C1 1-(3-bromophenyl)-2-(2-methylthiopyrimidin-4-yl)-ethanone (C1) 19.8 ml (140 mmol) diisopropylamine were dissolved in 250 ml dry tetrahydrofurane and cooled to -75 C. and 87.6 ml of a solution of n-butyllithium (1.6 M in hexane, 140 mmol) was added over a period of 20 minutes. After stirring for 15 minutes at -75 C. a solution of 13.1 g (93 mmol) <strong>[14001-63-9]2-methylthio-4-methylpyrimidine</strong> in 80 ml dry tetrahydrofurane was added within 30 minutes at -75 C. and the mixture was stirred for additional 15 minutes. Then a solution of 25.1 g (103 mmol) B1 was added within 30 minutes at -75 C. The mixture was allowed to warm up to room temperature and was poured on 600 ml ethyl acetate/water (1:1). The aqueous layer was extracted with 50 ml ethyl acetate and the combined organic layers were dried over sodium sulphate. Removal of the solvent in vacuo yielded 23.3 g (77%) C1, m.p. 98-101 C. MS: M=325 (ESI+), M=323 (ESI-). 1H-NMR (250 MHz, CDCl3): "enole" (75%) delta=2.62 (s, 3H, SCH3), 5.97 (s, 1H, CH=C), 6.66 (s, 1H, 5-H-pyrimidine), 8.34 (d, 1H, 6-H-pyrimidine), 14.7 (s, 1H, OH). "keto" (25%) delta=2.52 (s, 3H, SCH3), 4.35 (s, 2H, CH2), 6.97 (d, 1H, 5-H-pyrimidin), 8.46 (d, 1H, 6-H-pyrimidin).

Reference： [1]Patent: US2003/199691,2003,A1 .Location in patent: Page/Page column 13

33
[ 646528-36-1 ]
[ 14001-63-9 ]
[ 646528-13-4 ]

Yield	Reaction Conditions	Operation in experiment
		To the solution of 85 mL of diisopropylamine (Fluka 38300) and 2.5 L [OF THF AT-75C] under Argon is added 370 mL (0.55 Mol) of butyl lithium (BuLi; 1.6N in hexanes; Fluka 20160) within 1 h. To this is added 71 g (0.5 Mol) of [4-METHYL-2-METHYLSULFANYL-PYRIMIDINE] in 250 mL of [CH2CI2] [AT-75C] within 30 min. After this, a solution of 118 g (0.5 Mol) of 2, [4-DICHLORO-N-] methoxy-N-methyl-benzamide in 250 mL of CH2CI2 [AT-75C] within 30 min followed by letting the mixture warm up to rt. After completion, the reaction mixture is poured onto 7 L of [NH4CI] satd. and extracted with ethyl acetate. The combined organic layers are washed with brine, dried and evaporated. The crude product is suspended in hexanes. After filtering off and drying 1-(2,4-dichloro-phenyl)-2-(2-methylsulfanyl-pyrimidin-4-yl)-ethanone is obtained as yellow crystals. Title compound: m. p.: [105-107C] ; ES-MS: 313.0/314. 9 [M+H] [+.]

Reference： [1]Patent: WO2004/5282,2004,A1 .Location in patent: Page 47-48

34
[ 14001-63-9 ]
[ 68-12-2 ]
[ 1111637-80-9 ]

Yield	Reaction Conditions	Operation in experiment
100%		Preparation of (E)-3-hydroxy-2-(2-(methylthio)pyrimidin-4-yl)acrylaldehyde (3)2 3To a solution of DMF (114.9 g, 1.57 mol) in CHCI3 (800 mL) was added dropwise oxalyl chloride(190.3 g, 1.50 mol) at O0C. After the addition, the resulting mixture was warmed at 3O0C and stirred for 1.5 h. The mixture was allowed to cool to O0C and 4-methyl-2-(methylthio)pyrimidine (2) (100 g, 0.714 mol) was added to the mixture. The resulting mixture was warmed to 4O0C and stirred for 16 h. The reaction <n="59"/>mixture was cooled to room temperature and filtered. The cake was washed with CHCI3 (150 mLchi3) and dried in vacuum to give (E)-3-hydroxy-2-(2-(methylthio)pyrimidin-4-yl)acrylaldehyde (3) (342.0 g, 100%) as a yellow solid.

Reference： [1]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 40; 57-58

35
[ 14001-63-9 ]
[ 1083181-12-7 ]
[ 1111638-52-8 ]

Yield	Reaction Conditions	Operation in experiment
58.5%		Preparation of 2-(2-(methylthio)pyrimidin-4-yl)-1 -(1 -(phenylsulfonyl)-i H-pyrrolo[2,3-b]pyridin-5- yl)ethanone (G-1-3)n-BuLi (2.5 M, 93 mL, 0.233 mol) was added drop-wise to a solution of i-Pr2NH (32.5 mL, 0.233 mol) in dry THF (420 mL) at -780C and the resulting solution was stirred at -780C for 30 min. Then, a solution of 4- methyl-2-(methylthio)pyrimidine (22.33 g, 0.16 mol) in dry THF (110 mL) was added drop-wise and the resulting mixture was stirred at -780C for another 30 min. A solution of compound G-1-2 (50.0 g, 0.145 mol) in dry THF (250 mL) was then added drop-wise at -11O0C. After the addition, the resulting mixture was stirred at -11O0C for 10 min. TLC (hexane: EtOAc 1 :1 ) indicated the reaction was complete. EtOAc (300 mL) and H2O (300 mL) were added to the reaction mixture to quench the reaction. The organic layer was separated and the aq. layer was extracted with EtOAc (300 mLx3). The combined organic layers were washed with saturated aqueous NaCI (500 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (CH2CI2) to give compound 7 (36.0 g, 58.5%) as a yellow solid.

Reference： [1]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 112

36
[ 14001-63-9 ]
[ 14372-26-0 ]
[ 1142275-06-6 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 1377 - 1380

37
[ 14001-63-9 ]
[ 189442-78-2 ]
[ 1160000-91-8 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 2552 - 2554

38
[ 35071-17-1 ]
[ 74-88-4 ]
[ 14001-63-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium hydroxide; In ethanol; water; for 2h;	Step A: 4-Methyl-2-(methylthio)pyrimidine; The starting 4-methyl-2(1H)-pyrimidinethione (32.5 g, 0.2 mol) was dissolved in a mixture of EtOH (300 ml_), NaOH (15 g) and H2O (370 ml_). To this solution, methyliodide (26 g, 0.18 mol) was added. After 2 h, the reaction was complete. Then it was evaporated to remove EtOH. The reaction mixture was extracted with Et2O (400 ml_, 200 ml_, 200 ml_). The total organic phase was washed with H2O, and brine. After drying by Na2SO4, it was evaporated. The purification was done by distillation at 50 0C under < 1 mm Hg. Yield: 19.8 g (71%). 1H-NMR (400MHz, CDCI3) delta 8.39 (d, 1 H), 6.84 (d, 1 H), 2.59 (s, 3 H), and 2.48 (s, 3 H); LC/MS: m/z 141 (M+1) +.

Reference： [1]Patent: WO2009/76140,2009,A1 .Location in patent: Page/Page column 264

39
[ 14001-63-9 ]
[ 618-95-1 ]
[ 1160624-74-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With lithium hexamethyldisilazane; In tetrahydrofuran; at 0℃; for 12h;Product distribution / selectivity;	Step A: 2-[2-(Methylthio)-4-pyrimidinyl]-1 -(3-nitrophenyl)ethanone; <n="210"/>To a solution containing 10 g (71 mmol) of 4-methyl-2-(methylthio)pyrimidine, 12.9 g (71 mmol) of m-nitromethylbenzoate, and 65 mL of THF at O0C was slowly added 142 mL (142 mmol) of a 1.0 M solution of LHMDS in hexanes. The reaction mixture was allowed to stir at O0C for 12 h, then quenched by the addition of 2.0 M aqueous HCI. After 3 h, the resulting mixture was filtered and the filtercake was collected and recrystalized from EtOH to give 8.9 g (43 %) of the title compound of Step A as a yellow solid: 1H-NMR (CDCI3, 400 MHz) delta 8.66 (s, 1 H), 8.38 (d, 1 H, J = 5.5 Hz), 8.27 (d, 1 H, J = 8.1 Hz), 8.15 (d, 1 H, J = 7.7 Hz), 7.59 (t, 1 H, J = 7.8 Hz), 6.71 (d, 1 H1 J = 5.3 Hz), 6.07 (s, 1 H), and 2.62 (s, 3 H).

Reference： [1]Patent: WO2009/76140,2009,A1 .Location in patent: Page/Page column 208-209

40
[ 14001-63-9 ]
[ 547-63-7 ]
[ 1160105-52-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of diisopropylamine (10.1 ml_, 71.8 mmol) in anhydrous THF (50 ml_) is added n-butyllithum (33.6 mL of an 1.6M in hexane) dropwise at 0 0C. After 30 min at 0 0C, 4-methyl-2-(methylthio)pyrimidine (5 mL, 35.9 mmol) is added. The resulting mixture is stirred at 0 0C for 30 min. After the addition of <n="69"/>methyl isobutyrate (4.3 ml_, 37.7 mmol) at 0 0C, the reaction mixture is stirred overnight. The reaction mixture is quenched with acetic acid at 0 0C, diluted with water, and extracted with ethyl ether. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/heptane 7:93 to 40:60) to give 4.3 g of 3-methyl-1 - (2-methylsulfanyl-pyhmidin-4-yl)-butan-2-one. LCMS: 211.1 (M+H)+

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7938 - 7957
[2]Patent: WO2009/71701,2009,A1 .Location in patent: Page/Page column 67-68
[3]Tetrahedron Letters,2009,vol. 50,p. 5762 - 5764

41
[ 14001-63-9 ]
(3-ethoxycarbonylbenzyl)zinc chloride * lithium chloride [ No CAS ]
[ 1187334-97-9 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4228 - 4231

42
[ 14001-63-9 ]
[ 850056-55-2 ]
[ 850056-58-5 ]
C₁₉H₁₇N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example C1 1-(3-(2-pyridinylmethyloxy)phenyl)-2-(2-methylthiopyrimidin-4-yl)-ethanone (C1) 2.1 ml (15 mmol) diisopropylamine were dissolved in 70 ml dry tetrahydrofuran and cooled to -75 C. and 9.4 ml of a solution of n-butyllithium (1.6 M, 15 mmol) were added over a period of 10 minutes. After stirring for 15 minutes at -75 C. a solution of 1.69 g (12 mmol) <strong>[14001-63-9]2-methylthio-4-methylpyrimidine</strong> in 5 ml dry tetrahydrofuran was added within 10 minutes at -75 C. and the mixture was stirred for additional 15 minutes. Then a solution of 2.73 g (7 mmol) B3 (70% purity) in 5 ml dry tetrahydrofuran was added within 10 minutes at -75 C. The mixture was stirred for one hour at -75 C. and then allowed to warm up to room temperature and finally poured on 100 ml ethyl acetate/water (1:1). The aqueous layer was extracted with 50 ml ethyl acetate and the combined organic layers were dried over sodium sulphate. Removal of the solvent in vacuo and column chromatography on Silica (n-heptane/ethyl acetate 3:1) yielded 1.52 g (62%) C1. (keto-enole ratio measured by NMR in CDCl3 at 400 MHz is about 30:70). MS: M=352 (API+), 350 (API-)

Reference： [1]Patent: US2005/85473,2005,A1 .Location in patent: Page/Page column 8

43
[ 14001-63-9 ]
[ 1129-35-7 ]
[ 1202765-86-3 ]

Yield	Reaction Conditions	Operation in experiment
90.8%		To a solution of sodium bis(trimethylsilyl) amide (2 M sol. in THF, 79 mL) was added a solution of 4-methyl-2-(methylthio)pyrimidine (10 g, 71.32 mmol) in THF (20 mL) at 0 0C, and the resulting solution was stirred at 0 0C for 40 minutes. A solution of methyl 4- cyanobenzoate (11.49 g, 71.32 mmol) in THF (30 mL) was then added dropwise over 10 minutes to the mixture, and the mixture was stirred while attaining ambient temperature over 2 hours. The reaction was quenched by addition of sat'd aq. NH4Cl (100 mL) and extracted into ethyl acetate (250 mL x 2), and the combined organic layers were washed with brine (200 mL x 1), dried over Na2SO4, filtered and concentrated under reduced pressure to give a red solid. The red solid was suspended in hexane (150 mL), sonicated, filtered, and washed with hexane (200 mL) to give 4-(2-(2-(methylthio)pyrimidin-4-yl)acetyl)benzonitrile (A.120) (17.43 g, 90.8% yield) as an orange solid. The product was carried on without purification for the next step: Mass Spectrum (ESI) m/e = 270.1 (M+ 1).

Reference： [1]Patent: WO2009/158011,2009,A1 .Location in patent: Page/Page column 70-71

44
[ 14001-63-9 ]
[ 1128-76-3 ]
1-(3-chlorophenyl)-2-(2-methylthiopyrimidin-4-yl)-ethanone [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5689 - 5692

45
[ 14001-63-9 ]
[ 6919-61-5 ]
[ 340042-28-6 ]

Reference： [1]Monatshefte fur Chemie,2009,vol. 140,p. 423 - 430

46
[ 14001-63-9 ]
[ 52898-49-4 ]
[ 875757-74-7 ]

Reference： [1]Monatshefte fur Chemie,2009,vol. 140,p. 423 - 430

47
[ 14001-63-9 ]
C₈H₆ClNZn*ClLi [ No CAS ]
[ 1217817-62-3 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 2131 - 2133

48
[ 14001-63-9 ]
[ 51934-41-9 ]
[ 1254076-17-9 ]

Reference： [1]Synthesis,2010,p. 2853 - 2858

49
[ 14001-63-9 ]
[ 145959-21-3 ]
1-(3-chlorophenyl)-2-(2-methylthiopyrimidin-4-yl)-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		A solution of 2-methylthio-4-methylpyrimidine (5.6 g, 40.0 mmol) in anhydrous tetrahydrofurane (40 mL) was cooled EPO <DP n="128"/>to -78 C and a 1.8M lithium diisopropylamide-hexane solution (25 itiL, 45.1 ramol) was added thereto dropwise while stirring. After completion of dropwise addition, the mixture was stirred for 30min, then, a solution of 3-chloro- N-methoxy-N-methylbenzylamide (8.0 g, 40.0 mmol) in anhydrous tetrahydrofurane (8 mL) was added thereto dropwise, After completion of dropwise addition, the temperature was raised to room temperature, water (50 mL) was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over MgSO4 and the solvent was evaporated. The residue was recrystallized from tert-butyl methyl ketone/hexane to give the title compound (9.2 g, 33 mmol, yield 83%).1H-NMR (CDCl3) delta: 2.63 (s, 3H), 5.98 (s, IH), 6.68 (d, IH), 7.40 (m, 2H), 7.71 (m, IH), 7.83 (m, IH), 8.35 (d, IH). Since keto-enol tautomers exist based on pH values, there are two sets of signals.

Reference： [1]Patent: WO2006/137658,2006,A1 .Location in patent: Page/Page column 125-126

50
[ 14001-63-9 ]
[ 108593-44-8 ]
[ 950525-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane; In tetrahydrofuran; at 20℃; for 16h;	To a solution of methyl 3-methoxy-5-methylbenzoate (4.66 g, 25.86 mmol) and 4-methyl-2-(methylthio)-pyrimidine (4.32 mL, 31.03 mmol) in tetrahydrofuran (100 mL) was dropwise added lithium hexamethyldisilazide (50.68 mL, 50.68 mmol, 1M solution in THF). The reaction mixtue was stirred at 20 C. for 16 hours. After completion of the nucleophilic attack reaction, the reaction mixture was neutralized with a saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated by vacuum distillation, and the concentrate containing the title compound was used in the next reaction without further purification.1H NMR (300 MHz, CDCl3) delta 2.39 (s, 3H), 2.54 (s, 3H), 3.84 (s, 3H), 4.36 (s, 2H), 6.96-6.99 (m, 2H), 7.37 (s, 1H), 7.46 (s, 1H), 8.45 (d, J=5.04 Hz, 1H); IR (KBr) 3425, 1568, 1311, 837 cm-1.

Reference： [1]Patent: US2011/15395,2011,A1 .Location in patent: Page/Page column 17
[2]Russian Journal of Organic Chemistry,2020,vol. 56,p. 514 - 520
Zh. Org. Khim.,2020,vol. 56,p. 514 - 520,7

51
[ 14001-63-9 ]
[ 2868-37-3 ]
[ 1256963-04-8 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7938 - 7957

52
[ 14001-63-9 ]
[ 3282-30-2 ]
[ 1256963-06-0 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7938 - 7957

53
[ 14001-63-9 ]
[ 1353575-24-2 ]
[ 1353575-57-1 ]

Yield	Reaction Conditions	Operation in experiment
81%		To a cooled solution of 4-methyl-2-(methylthio)pyrimidine (1.26 mL, 9.04 mmol) and methyl 2-chloro-5-fluoro-3-pivalamido-benzoate (/, 2.0 g, 6.95 mmol) in THF (35 mL) at 0 C, LiHMDS (1.0 M in THF, 25.7 mL, 25.7 mmol) was slowly added. The reaction was maintained at 0 C for 2 h. LCMS of reaction aliquot indicated complete conversion and the reaction was quenched by the addition of 1.0 M aqueous HC1 solution. The resulting mixture was stirred for 1 h at rt, whereupon EtOAc was then added and the resulting biphasic mixture was neutralized to pH 8 with saturated aqueous NaHC03 solution. The two phases were separated and aqueous phase was extracted with EtOAc. The organic phases were combined, washed with brine, dried (Na2S04), and concentrated. The resulting residue was adsorbed onto silica gel and was purified by flash chromatography on silica gel using an EtO Ac-heptane (0-30%) elution gradient to give N-(2-chloro-5-fluoro-3-(2-(2- (methylthio)pyrimidin-4-yl)acetyl)phenyl)pivalamide (2.24 g, 5.66 mmol, 81 % yield) as a yellow solid: 1H NMR (300 MHz, CDC13) delta ppm 1.37 (s, 9 H) 2.62 (s, 3 H) 5.70 (s, 1 H) 6.64 (d, J=5.6 Hz, 1 H) 7.03 (dd, J=8.2, 2.3 Hz, 1 H) 8.27 (br. s., 1 H) 8.36 (d, J=5.3 Hz, 1 H) 8.41 (dd, J=10.6, 2.93 Hz, 1 H).

Reference： [1]Patent: WO2011/161216,2011,A1 .Location in patent: Page/Page column 36-37

54
[ 14001-63-9 ]
[ 140-11-4 ]
1-[2-(methylsulfanyl)pyrimidin-4-yl]propan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Prepartion of intermediate l-(2-Methylsulfanyl-pyrimidin-4-yl)-propan-2-(17)To a solution of 4-Methyl-2-(methylthio)pyrimidine (1) (3 g, 21.40 mmol) in THF (35.7 mL) at -10 C was added LHMDS (32.1 mL, 32.1 mmol, 1M in THF). The resulting reaction was warmed to rt and stirred for 15 minutes, after which time the reaction was cooled back to -10C and Benzyl Acetate (3.21 mL, 23.54 mmol) was added. The reaction was then warmed to rt and stirred for 1 hour, after which time complete conversion to product was observed by LCMS. TLC after 1 hour still showed the presence of some starting material and the reaction was continued stirring for an additional hour. After this time there was no change in TLC and the reaction was worked up. The reaction was quenched by slow addition of saturated ammonium chloride and the volatile solvent evaporated. The mixture was then diluted with EtOAc and water. The organic layer was then washed with brine, dried with sodium sulfate, andconcentrated. The crude residue was purified by flash chromatography with a gradient of 8-66% EtOAc in Heptane to give the desired product as a yellow liquid (1.93g, 50%). MS (ES+): m/z = 183.1 (100) [MH+]. HPLC: tK = 0.91 minute over 3 minutes. Purity: 76% [HPLC (LC/MS) at 220 nm].

Reference： [1]Patent: WO2012/85815,2012,A1 .Location in patent: Page/Page column 77-78

55
[ 14001-63-9 ]
[ 1383716-33-3 ]

Reference： [1]Patent: WO2012/85815,2012,A1

56
[ 14001-63-9 ]
[ 227322-00-1 ]
[ 1383716-74-2 ]

Yield	Reaction Conditions	Operation in experiment
85.8%		Step 2: To a solution of 4-methyl-2-methylsulfanyl-pyrimidine (9.00 g, 64.19 mmol, 1.00 eq) in THF (500 mL) was added LDA (2 M, 48.46 mL, 1.51 eq) at -78C. After stirring for 1 h, a solution of compound 2 (13.79 g, 96.29 mmol, 1.50 eq) in THF (500 mL) was added drop wise at -78 C and then the reaction mixture was stirred at -78 C for 4 h. Quenched with saturated aq. NH4CI (100 mL), the aqueous phase was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SC, filtered and concentrated. The residue was crystallized from petroleum ether/ethyl acetate to afford the desired compound 4 (13.60 g, 55.06 mmol, 85.8% yield) as a yellow solid. LCMS: RT = 0.629 min, m/z 223.0 [M+H]+.
		Preparation of intermediate l-Cyclopropyl-3-[2-(methylsulfanyl)pyrimidin-4- yl]propan-2-one (2):To a solution of 4-methyl-2-(methylthio)pyrimidine (5.63 mL, 40.4 mmol) in THF (20 mL) at -10 C, LiHMDS (60.6 mL, 60.6 mmol) (IN in MBTE) was added dropwise under nitrogen. The reaction mixture coagulated, and stopped stirring. For this, additional THF (40 mL) was added to dissolve the highly viscous mixture. The reaction was warmed up to rt and was stirred for 30 minutes. The reaction mixture was re-cooled to -10C, then 2-cyclopropyl-N-methoxy-N-methylacetamide (7.47 g, 40.4 mmol) was added dropwise. The reaction mixture was warmed up to rt, then stirred for an additional 2 hours. The reaction was partitioned between ammonium chloride solution and EtOAc. The organic layer was separated, and the aqueous layer was back-extracted. The organic extracts were combined, washed with brine, dried over sodium sulfate, then concentrated in vacuo. The crude product was purified by Biotage silica gel chromatography [lOOg SNAP column, 10% EtO Ac/heptane to 100% EtOAc] to obtain the desired product, which was still contaminated significantly with the starting material, 4-methyl-2- (methylthio)pyrimidine (5.63 g, 48% yield). The product was carried on to the next step without further purification. MS (ES+): m/z = 223.2/224.3 (100/50) [MH+]. HPLC: tR = 0.84 minute over 3 minutes. Purity: 77% [HPLC (LC/MS) at 220 urn].

Reference： [1]Patent: WO2017/21969,2017,A1 .Location in patent: Page/Page column 30
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 72 - 76
[3]Patent: WO2012/85815,2012,A1 .Location in patent: Page/Page column 35

57
[ 14001-63-9 ]
[ 765-85-5 ]
C₁₁H₁₄N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane In tetrahydrofuran at 60℃; for 96h;

Reference： [1]Wityak, John; McGee, Kevin F.; Conlon, Michael P.; Song, Ren Hua; Duffy, Bryan C.; Clayton, Brent; Lynch, Michael; Wang, Gwen; Freeman, Emily; Haber, James; Kitchen, Douglas B.; Manning, David D.; Ismail, Jiffry; Khmelnitsky, Yuri; Michels, Peter; Webster, Jeff; Irigoyen, MacArena; Luche, Michele; Hultman, Monica; Bai, Mei; Kuok, Iokteng D.; Newell, Ryan; Lamers, Marieke; Leonard, Philip; Yates, Dawn; Matthews, Kim; Ongeri, Lynette; Clifton, Steve; Mead, Tania; Deupree, Susan; Wheelan, Pat; Lyons, Kathy; Wilson, Claire; Kiselyov, Alex; Toledo-Sherman, Leticia; Beconi, Maria; Muñoz-Sanjuan, Ignacio; Bard, Jonathan; Dominguez, Celia [Journal of Medicinal Chemistry, 2015, vol. 58, # 7, p. 2967 - 2987]

58
[ 14001-63-9 ]
[ 2868-37-3 ]
C₁₀H₁₂N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane In tetrahydrofuran at 60℃; for 96h;

59
[ 14001-63-9 ]
[ 116022-18-5 ]
[ 616196-43-1 ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2016,vol. 31,p. 111 - 122

60
[ 14001-63-9 ]
C₈H₁₅NO₂ [ No CAS ]
C₁₂H₁₆N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 4: To a solution of 53_4 (4.50 g, 32.09 mmol, 1.00 eq) in THF (225 mL) was added LDA (2 M, 24.07 mL, 1.50 eq) at -78C. After stirred for 1 hr, a solution of 2- cyclobutyl-N-methoxy-N-methyl-acetamide (6.05 g, 38.51 mmol, 1.20 eq) in THF (120 mL) was added into it at -78C. The resulting mixture was sitrred at -78C for 4 hr, quenched with saturated NH4CI (200 mL), and the aqueous phase was extracted with ethyl acetate (200 mL*3). The combined layers were washed with brine (200 mL), dried over anhydrous Na2SO t, filtered and concentrated to give 53_5 (10.00 g, crude) as a yellow oil. LCMS: RT = 0.788 min, m/z 237.1 [M+H]+

Reference： [1]Patent: WO2017/21969,2017,A1 .Location in patent: Page/Page column 63

61
[ 14001-63-9 ]
[ 68-12-2 ]
[(2E)-3-(dimethylamino)-2-[2-(methylsulfanyl)pyrimidin-4-yl]prop-2-en-1-ylidene]dimethylazanium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		Into a 100 mL 3-necked round-bottom flask, was placed a solution of oxalyl dichloride (6.6 mL, 2.00 equiv) in chloroform/N,N-dimethylformamide (45/6 mL) at 0 C. The above mixture was stirred for 30 min at 45 C. The reaction was cooled to 0 C. 4-methyl-2-(methylsulfanyl)pyrimidine (5.0 g, 142.65 mmol, 1.00 equiv) was added to the solution separately at 0 C. The resulting solution was stirred for 16 h at 45 C. in an oil bath. The solids were collected by filtration. This resulted in 8.5 g (90%) of [(2E)-3-(dimethylamino)-2-[2-(methylsulfanyl)pyrimidin-4-yl]prop-2-en-1-ylidene]-dimethylazanium as a yellow solid. LC-MS (ES+): m/z 250.95 [M+H+], tR=0.38 min, (1.9 minute run).

Reference： [1]Patent: US2017/8904,2017,A1 .Location in patent: Paragraph 0435-0436

62
[ 14001-63-9 ]
[ 4606-07-9 ]
[ 1256963-05-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

63
[ 14001-63-9 ]
[ 141-78-6 ]
1-[2-(methylsulfanyl)pyrimidin-4-yl]propan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.66 g		To a mixture of 4-methyl-2-(methylsulfanyl)pyrimidine (11.5 g) and THF (300 ml) was added dropwise lithium hexamethyldisilazide (1 M THF solution, 164 ml) under nitrogen atmosphere at 0 C. The mixture was stirred at 0 C. for 30 min, and to the reaction solution was added dropwise ethyl acetate (14.5 g) at 0 C. The mixture was allowed to warm to 30 C., and stirred at the same temperature for 15.5 hr. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (9.66 g). MS: [M+H]+ 183.0.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29
[2]Patent: US2019/300536,2019,A1 .Location in patent: Paragraph 0615-0616

64
[ 14001-63-9 ]
[ 2926-29-6 ]
C₇H₇F₃N₂S [ No CAS ]

Reference： [1]Science,2019,vol. 365,p. 360 - 366

65
[ 14001-63-9 ]
[ 275818-95-6 ]
C₇H₈F₂N₂S [ No CAS ]

Reference： [1]Nature Communications,2020,vol. 11

66
[ 14001-63-9 ]
[ 74385-37-8 ]
C₁₄H₁₃FN₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-methylthio-4-methylpyrimidine With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.5h; Inert atmosphere; Stage #2: methyl 4-fluoro-3-methoxy-benzoate In tetrahydrofuran at -70 - 20℃; for 6h; Inert atmosphere;	4.1.2.2. 1-(4-Fluoro or chloro)-3-methoxyphenyl)-2-(2-(methylthio)pyrimidin-4-yl)ethan-1-one (9-10). To a solution of and 4-methyl-2-(methylthio)pyrimidine (8, 771 mg, 5.5 mmol) in THF (20 mL)at 70 C, LiHMDS (11 mL, 1.0 M solution in THF, 10.8 mmol) wasslowly added under N2 to the reaction mixture maintaining thetemperature at 70 C. After 30 min, a solution of compound 6 or 7(5.0 mmol) in THF (10 mL) was slowly added to the reactionmixture under N2 at 70 C. The resulting mixture was stirred atroom temperature for 6 h. The mixture was quenched with saturatedaq. NH4Cl (20 mL), and ethyl acetate (30 mL) was added forextraction. The organic layer was separated, and the aqueous layerwas extracted with ethyl acetate (3 10 mL). The combined ethylacetate extract was washed with saline and dried over anhydroussodium sulfate, evaporated in vacuo to yield the title compounds 9and 10, which were subjected to the next step without furtherpurification.

Reference： [1]Ali, Eslam M.H.; El-Telbany, Rania Farag A.; Abdel-Maksoud, Mohammed S.; Ammar, Usama M.; Mersal, Karim I.; Zaraei, Seyed-Omar; El-Gamal, Mohammed I.; Choi, Se-In; Lee, Kyung-Tae; Kim, Hee-Kwon; Lee, Kwan Hyi; Oh, Chang-Hyun [European Journal of Medicinal Chemistry, 2021, vol. 215]

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Code	Phrase
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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. 14001-63-9 ] {[proInfo.proName]}

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[ 14001-63-9 ] Synthesis Path-Upstream 1~6

[ 14001-63-9 ] Synthesis Path-Downstream 1~66

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Sulfides

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Pyrimidines

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[ 14001-63-9 ]