16097-62-4|2-(Methylthio)-6-(trifluoromethyl)pyrimidin-4-ol| Ambeed

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Quality Control of [ 16097-62-4 ] Purity: 98% SDS Specification

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Product Details of [ 16097-62-4 ]

CAS No. :	16097-62-4
Formula :	C₆H₅F₃N₂OS
M.W :	210.18
SMILES Code :	OC1=NC(SC)=NC(C(F)(F)F)=C1
MDL No. :	MFCD00153191
InChI Key :	BRLPDRZKOMZVOY-UHFFFAOYSA-N
Pubchem ID :	135410006

Safety of [ 16097-62-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 16097-62-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 16097-62-4 ]

[ 16097-62-4 ] Synthesis Path-Downstream 1~35

1
[ 2524-04-1 ]
[ 16097-62-4 ]
[ 129409-73-0 ]

References: [1]Monatshefte fur Chemie,1990,vol. 121,p. 289 - 292.

2
[ 368-54-7 ]
[ 77-78-1 ]
[ 16097-62-4 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.

3
[ 16097-62-4 ]
[ 85730-38-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	With iron(III) chloride; sulfuryl dichloride; acetic anhydride; In acetic acid; at 110℃; for 6.0h;	A solution of 2- (methylthio) -6- (trifluoromethyl) pyrimidin-4-ol (210 mg, 1 mmol) in AcOH (3 mL) was added Ac2O (0.2 ml) , FeCl3 (40 mg) and SO2Cl2 (150 mg) . Then refluxed at 110 for 6 h. The reaction mixture was cooled to room temperature, and solvent was removed in vacuo. The residue was extracted by DCM and icy H2O 3 times. The organic layer was combined, washed with brine, dried over Na2SO4 and concentrated to give 110 mg of 5-chloro-2- (methylthio) -6- (trifluoromethyl) pyrimidin-4-ol (162-01) as a light yellow oid (45) . Mass (m/z) : 245.5 [M+H] +

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.
[2]Patent: WO2018/14802,2018,A1 .Location in patent: Paragraph 0452.

4
[ 16097-62-4 ]
[ 672-45-7 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.

5
[ 16097-62-4 ]
[ 16097-63-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trichlorophosphate; at 120℃; for 3.0h;	A solution of 2- (methylthio) -6- (trifluoromethyl) pyrimidin-4-ol (43-01) (1.4g, 6.67mmol) in POCl3 (15mL) was refluxed at 120 for 3hrs. The reaction mixture was cooled to room temperature, and POCl3 was removed in vacuo. The residue was extracted by DCM and icy H2O 3 times. The organic layer was combined, washed with brine, dried over Na2SO4 and concentrated to give 1.38g of 4-chloro-2- (methylthio) -6- (trifluoromethyl) pyrimidine as a light yellow oid (90) . LC-MS (ESI) m/z: calcd for [C6H5ClF3N2S+] , 229.0, found 229.0.
	With thionyl chloride;N,N-dimethyl-formamide; In toluene; at 80℃; for 1.0h;	To a mixture of 20 ml of toluene, 5 g of 2-methylthio- 6-trifluoromethylpyrimidin-4-ol and 0.37 g of N, N- dimethylformamide, 5.7 g of thionyl chloride was slowly added dropwise at 800C. This mixture was stirred at 800C for 1 hour. The reaction mixture was left standing to cool to room1"temperature, poured into water and then extracted three times with tert-butyl methyl ether. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product. This crude product was used in the next step without purification.
	With trichlorophosphate; at 120℃; for 5.0h;Inert atmosphere;	2-(Methylthio)-6-(trifluoromethyl)pyrimidin-4-ol 13a (100 mg, 0.21 mmol) was dissolved in phosphorus oxychloride (20 mL). The reaction solution was reacted under a nitrogen atmosphere at 120C for 5 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure to obtain the title compound 13b (4 g, crude product) as a yellow solid, which was used directly in the next step without purification.

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 407 - 412.
[2]Patent: WO2018/14802,2018,A1 .Location in patent: Paragraph 0232.
[3]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.
[4]Patent: WO2010/134478,2010,A1 .Location in patent: Page/Page column 182.
[5]Patent: EP3889153,2021,A1 .Location in patent: Paragraph 0140; 0141.

6
[ 3731-53-1 ]
[ 16097-62-4 ]
2-[(pyridin-4-ylmethyl)-amino]-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

7
[ 64-04-0 ]
[ 16097-62-4 ]
2-phenethylamino-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

8
[ 104-86-9 ]
[ 16097-62-4 ]
2-(4-chloro-benzylamino)-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

9
[ 2393-23-9 ]
[ 16097-62-4 ]
2-(4-methoxy-benzylamino)-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

10
[ 62-53-3 ]
[ 16097-62-4 ]
2-phenylamino-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

11
[ 103-67-3 ]
[ 16097-62-4 ]
2-(benzyl-methyl-amino)-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

12
[ 100-46-9 ]
[ 16097-62-4 ]
2-benzylamino-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

13
[ 104-11-0 ]
[ 16097-62-4 ]
2-[(4-chloro-benzyl)-methyl-amino]-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

14
[ 4152-90-3 ]
[ 16097-62-4 ]
2-(3-chloro-benzylamino)-6-trifluoromethyl-pyrimidin-4-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

15
[ 368-54-7 ]
[ 74-88-4 ]
[ 16097-62-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4449 - 4452.

16
[ 16097-62-4 ]
[ 85730-36-5 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.

17
[ 16097-62-4 ]
[ 85730-32-1 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.

18
[ 16097-62-4 ]
[ 85730-33-2 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.

19
[ 16097-62-4 ]
[ 85730-43-4 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.

20
[ 16097-62-4 ]
[ 85730-40-1 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.

21
[ 16097-62-4 ]
[ 85730-39-8 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.
[2]Patent: WO2018/14802,2018,A1 .

22
[ 16097-62-4 ]
[ 16097-60-2 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 219 - 223.

23
[ 2986-19-8 ]
[ 372-31-6 ]
[ 16097-62-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydroxide; In ethanol; at 90℃; for 2.0h;Inert atmosphere; Microwave irradiation;	To a solution of ethyl 4, 4, 4-trifluoro-3-oxobutanoate (2g, 10.9mmol) and methyl carbamimidothioate (4g, 21.3mmol) in EtOH (10mL) was added 10N NaOH solution (2mL) dropwise under N2 atmosphere. The reaction mixture was microwaved at 90 for 2hrs. The reaction mixture was cooled to room temperature, then solvents were evaporated in vacuo. The residue was dissolved in H2O and acidified to PH2.0 with 1N HCl, then extracted by DCM 3 times. The organic layer was combined, washed with brine, dried over Na2SO4 and further purified by recrystalization with DCM/PE to give 1.8g of 2- (methylthio) -6- (trifluoromethyl) pyrimidin-4-ol as a white solid (43-01) (8.5mmol, 78) . 1H NMR (400 MHz, DMSO) : δ 6.59 (s, 1H) , 2.51 (s, 3H) .

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 407 - 412.
[2]Patent: WO2018/14802,2018,A1 .Location in patent: Paragraph 0217.

24
[ 16097-62-4 ]
1-benzyl-5-(2-(methylthio)-6-(trifluoromethyl)pyrimidin-4-yl)pyridin-2(1H)-one [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 407 - 412.
[2]Patent: WO2018/14802,2018,A1 .

25
[ 16097-62-4 ]
C₁₈H₁₃ClF₃N₃OS [ No CAS ]