672-47-9|2-(Trifluoromethyl)pyrimidine-4,6-diol| Ambeed

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Quality Control of [ 672-47-9 ] Purity: 97% SDS Specification

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Product Details of [ 672-47-9 ]

CAS No. :	672-47-9
Formula :	C₅H₃F₃N₂O₂
M.W :	180.08
SMILES Code :	OC1=CC(O)=NC(=N1)C(F)(F)F
MDL No. :	MFCD02678234
InChI Key :	AMGBKPNVGVAFEN-UHFFFAOYSA-N
Pubchem ID :	243103

Safety of [ 672-47-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301
Precautionary Statements:	P301+P310
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of [ 672-47-9 ]

* 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.

Downstream synthetic route of [ 672-47-9 ]

[ 672-47-9 ] Synthesis Path-Downstream 1~35

3
[ 108-13-4 ]
[ 383-63-1 ]
[ 672-47-9 ]

Yield	Reaction Conditions	Operation in experiment
44.4%	With NaH; In toluene; mineral oil; butan-1-ol;	EXAMPLE 3 4,6-Dihydroxy-2-trifluoromethylpyrimidine, Compound VI, starting material for Step 2 Sodium hydride (900 g, 57.5% dispersion in mineral oil; 518 g active NaH; 22.5M) was stirred with 7.5 L toluene in a 22 L round-bottomed flask. Butanol was added over 5 hr. so that the pot temperature was maintained at 40. The mixture was stirred an additional 16 hr. Malonamide (765 g; 7.5 M) was added, followed by ethyl trifluoroacetate (1065 g; 7.5 M). The ensuing reaction was exothermic; the mixture was then heated on a steam-bath for 3.5 hrs. It was then stirred at 23-25 for an additional 16 hrs. The mixture was extracted with water (14 L and 12 L). The combined aqueous extracts were treated with activated charcoal and filtered. The filtrate was maintained at 10-15 as it was acidified to pH 1-2 with 37% hydrochloric acid. The mixture was chilled to 5. The solid was isolated by filtration and dried at 50 in vacuo to give 600 g (44.4% yield) VI m.p. 255-256 (Lit. 265).
		To a suspension of 60% NaH in oil (11.7 g) in toluene (98 mL) was added BuOH (21. 8 g). The mixture was stirred at ambient temperature for 16 hr. To the mixture were added malonamide (10.0 g) and trifluoro-acetic acid ethyl ester (13.9 g). The mixture was stirred at 100C for 3.5 hr and ambient temperature for 16 hr. The organic layer was extracted with water (two times) and the aqueous layer was filtrated through activated carbon. To the aqueous layer was added conc. HCI (pH 1) and the suspension was stirred at 4C for 2 hr. The precipitate was collected by filtration and dried at 80C under reduced pressure to give 2-trifluoromethyl-pyrimidine-4, 6-diol (3.25 g). ESI MS m/e 178, M-H+ ;'H NMR (300 MHz, CDC13) 8 6.00 (s, 1 H), 12.48 (brs, 2 H).

References: [1]Patent: US4963678,1990,A .
[2]Patent: WO2005/95357,2005,A2 .Location in patent: Page/Page column 140.
[3]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 171 - 176.

4
[ 672-47-9 ]
[ 705-24-8 ]

Yield	Reaction Conditions	Operation in experiment
78.8%	With trichlorophosphate; In water; triethylamine;	EXAMPLE 2 4,6-Dichloro-2-trifluoromethylpyrimidine, Compound V, Step 2 4,6-Dihydroxy-2-trifluoromethylpyrimidine (VI; 540 g; 3.0 M) was stirred with phosphorous oxychloride (1300 mL; 2147 g; 14.0 M) in a 5 L round-bottom flask with mechanical stirrer and triethylamine (607 g; 6.0 M) was added over 1 hr. After the exotherm, the reaction was heated on a stem-bath for 3 hr. The reaction mixture was cooled to 40, and then it was poured with stirring into a mixture of 10 kg ice and 2 kg water. The mixture was extracted with 4*0.5 L methylene chloride. The combined extracts were dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give the crude compound V. When further purification was desired, the crude V was distilled at 48-50/2 mm using a steam-bath (Lit. b.p. 38/1 mm) to give a colorless liquid. The purified yield was 78.8%. Anal. Calcd. for C5 HCl2 F3 N2: C, 27.68; H, 0.47; N, 12.91. Found: C, 27.45; H, 0.39; N, 12.86.
	With triethylamine; trichlorophosphate; at 120℃; for 3h;	To a suspension of 2-trifluoromethyl-pyrimidine-4, 6-diol (3.25 g) in POC13 (7.89 mL) was added Et3N (5.00 mL). The mixture was stirred at 120C for 3 hr, cooled to ambient temperature, and poured into ice water. The aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtrated, and concentrated under reduced pressure to give 4, 6-dichloro-2-trifluoromethyl-pyrimidine. To the solution of the above material (1.00 g) in THF (10 mL) were added iPrzNEt (0.98 mL) and 50% aqueous Me2NH (0.48 mL). The mixture was stirred at ambient temperature for 60 hr. To the solution was added saturated aqueous NaHCO3 and the aqueous layer was extracted with CHCI3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure, and purified by medium-pressure liquid chromatography (silica gel, 5% to 25% EtOAc in hexane) to give (6-chloro-2- trifluoromethyl-pyrimidin-4-yl)-dimethyl-amine (728 mg). ESI MS m/e 225 M+ ; 1H NMR (300 MHz, CDC13) 8 2.77-3. 61 (m, 6 H), 6.50 (s, 1 H).
31.4 g	With triethylamine; trichlorophosphate; at 5 - 105℃; for 4h;	To the reaction flask was added phosphorus oxychloride 144.1 g,Stirring 2-trifluoromethyl-4, 6-dihydroxypyrimidine 36g, stirring,Cooling to 5 ~ 10 C dropping triethylamine 55.4 mL, dropwise warming to 100 ~ 105 C for 4 hours,After the control reaction qualified, the control 0 ~ 5 The reaction solution was added to ice water, after stirring,Then add dichloromethane and stir the layers, add methylene chloride in the aqueous phase to extract, combine the organic phases, wash,Filtration and drying gave the crude product. The crude product was distilled to collect the steamed product, 31.4 g of a colorless liquid,Yield 72.4%, HPLC 99.9%.

References: [1]Patent: US4963678,1990,A .
[2]Patent: WO2005/95357,2005,A2 .Location in patent: Page/Page column 140; 141.
[3]Patent: CN106883185,2017,A .Location in patent: Paragraph 0018.

5
[ 354-38-1 ]
[ 105-53-3 ]
[ 672-47-9 ]

Yield	Reaction Conditions	Operation in experiment
21%		Example 4 :2-(trifluoromethyl)pyrimidine-4,6-diol:; 4.11 g of sodium (178.5 mmoles, 1.05 eq.) were added portionwise to 140 mL of EtOH. After completion of the reaction, 31 mL (204 mmoles, 1.20 eq.) of diethylmalonate were added followed by 15 mL (170.0 mmoles, 1.0 eq.) of 2,2,2-trifluoroacetamide. The mixture was EPO <DP n="27"/>refluxed for 3h. Solvents were removed under reduced pressure and the crude mixture was poured into 115 mL of water. The resulting solution was acidified with aqueous HCI 6N. The resulting precipitate was filtered off, triturated with 50 mL of benzene and dried under vacuum at 40C to give 6.5 g of a white solid.Yield : 21 %LC-MS : Tr = 2.82 min. (88 %) (ES-MS: m/z 181.0 (M+H)) [Column : Nucleosil C-18HD, 4x70 mm, 3μm, gradient CH3CN/H2O/TFA 0.05% : 5-100% CH3CN (6 min.), 100% CH3CN (1.5 min.), flow : 1 mL/min]. 1H-NMR (DMSO-D6, 400 MHz) δ : 6.00 (s, 1H).13C-NMR (DMSO-D6, 100 MHz) δ : 90.6 ; 120.0 (q, J = 259.8 Hz) ; 154.8 (q, J = 32.5 Hz) ;172.2.19F-NMR (DMSO-D6, 377 MHz) δ : -48.6.

References: [1]Patent: WO2006/136442,2006,A1 .Location in patent: Page/Page column 25-26.

6
[ 672-47-9 ]
[ 652-62-0 ]

Yield	Reaction Conditions	Operation in experiment
		5-Nitro-2-(trifluoromethyl)pyrimidine-4,6-diol (16) Dihydroxypyrimidine 15 (1.0 g, 5.6 mmol) was dissolved in TFA (2 mL) and stirred for 15 min at RT. Fuming nitric acid (0.325 mL) was added drop-wise, maintaining the temperature <25C, and the reaction was stirred overnight. Water was added to the reaction mixture, which was then extracted with ethyl acetate (2 x 20 mL). The organic extracts were dried over MgS04, filtered and concentrated to provide 851 mg of nitropyrimidine 16 as an off-white solid. LCMS m/z 224.1 (M+1 ). 9F NMR (376 MHz, DMSO-cfe) δ -70.45 (s, 3 F).
	With nitric acid; at 4 - 6℃; for 1.5h;	6-chloro-5-nitro-2-(trifluoromethyl)pyrimidin-4-ol:; 58 %5 mL (122.2 mmoles, 11 eq.) of fuming HNO3 were cooled at +4C (int. T). Then 2 g (11.11 mmoles, 1.0 eq.) 2-(trifluoromethyl)pyrimidine-4,6-diol of were added portionwise in order to maintain the temperature between +4 and +6C. After completion of the addition, the solution was stirred at +4C for 1.5h. The mixture was poured into 25 mL of iced water and the aqueous solution was stirred for 20 min. The solution was then evaporated under reduced pressure to dryness. The resulting solid was dried under vacuum overnight to give 2.72 g of a yellow solid. This compound was used in the next step without further purifications.LC-MS : Tr = 2.10 min. (95.7 %) (no ionization) [Column : Nucleosil C-18HD, 4x70 mm, 3μm, gradient CH3CN/H2O/TFA 0.05% : 0-100% CH3CN (6 min.), 100% CH3CN (1.5 min.), flow : 1 mL/min]. EPO <DP n="28"/>13C-NMR (DMSO-D6, 100 MHz) δ : 118.7 (q, J = 258.1 Hz) ; 120.6 ; 151.9 (q, J = 32.2 Hz) ; 162.6.

References: [1]Patent: WO2011/58478,2011,A1 .Location in patent: Page/Page column 35-36.
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5721 - 5726.
[3]Patent: WO2006/136442,2006,A1 .Location in patent: Page/Page column 26-27.

7
[ 30414-53-0 ]
[ 672-47-9 ]
[ 1260235-94-6 ]

References: [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 171 - 176.

8
[ 672-47-9 ]
[ 715-46-8 ]

References: [1]Patent: WO2011/58478,2011,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5721 - 5726.
[3]Patent: WO2006/136442,2006,A1 .

9
[ 672-47-9 ]
[ 2344-17-4 ]

References: [1]Patent: WO2011/58478,2011,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5721 - 5726.

10
[ 672-47-9 ]
[ 1305117-36-5 ]

References: [1]Patent: WO2011/58478,2011,A1 .

11
[ 672-47-9 ]
[ 1305117-37-6 ]

References: [1]Patent: WO2011/58478,2011,A1 .

12
[ 672-47-9 ]
[ 1305115-74-5 ]

References: [1]Patent: WO2011/58478,2011,A1 .

13
[ 672-47-9 ]
[ 1305116-80-6 ]

References: [1]Patent: WO2011/58478,2011,A1 .

14
[ 672-47-9 ]
[ 1305115-80-3 ]

References: [1]Patent: WO2011/58478,2011,A1 .

15
[ 672-47-9 ]
[ 1305115-82-5 ]

References: [1]Patent: WO2011/58478,2011,A1 .

16
[ 108-13-4 ]
[ 431-47-0 ]
[ 672-47-9 ]

Yield	Reaction Conditions	Operation in experiment
		-(Trifluoromethyl)pyrimidine-4,6-diol (15) Sodium hydride (57 g of a 60% dispersion in mineral oil, 1430 mmol) was stirred in toluene under nitrogen and cooled with a wet ice bath. Butanol (130 mL, 1430 mmol) was added drop-wise and mixture was stirred for 30 min.Malonamide (50 g, 480 mmol) was added in one portion followed by the drop-wise addition of methyl trifluoroacetate (14) (67.5 g, 475 mmol), which led to an immediate exotherm. When the addition was complete, the reaction mixture was stirred at 40 C overnight and then cooled to RT. The reaction was diluted with 1 N HCI (300 mL) and then concentrated HCI was added until pH = 2. The layers were separated and the aqueous layer was extracted with ethyl acetate (3X), dried over magnesium sulfate, and concentrated. The resulting orange solid was triturated with 2:1 heptane: DCM (2 x 100 mL), collected by filtration, and dried under vacuum overnight to provide 28.1 g of 15 as a light orange solid. LCMS m/z 181.1 (M+1 ). H NMR (400 MHz, CD3OD) δ 5.90 (s, 1 H).
		To the reaction flask was added 500 mL methanol, cooled to 0 ~ 5 C, 118.6 g sodium methoxide was added,Stirring until substantially clear, adding 102.1g malonamide, stirring, warmed to 35 ,153.7 g of methyl trifluoroacetate was added, and after completion of the addition, the mixture was stirred for 30 minutes,The temperature was raised to 65 to 70 C and refluxed for 15 hours. After the reaction, cooling to 25 ~ 35 ,100 mL methyl tertiary ether was added dropwise and the temperature dropped to 5 ~ 10 C. After stirring, the filter cake was rinsed with ruthenium ether. After filtration, the solid was transferred to a single-necked flask and concentrated under reduced pressure. Add water, stir until clear, add concentrated hydrochloric acid to adjust pH = 1 ~ 2, filter to obtain filter cake 95g. The filter cake was added with 250 mL of ethyl acetate, heated to reflux, stirred, filtered and concentrated under reduced pressure to constant weight to give 118.4 g of an off-white solid in a yield of 65.8% and HPLC of 94.3%.

References: [1]Patent: WO2011/58478,2011,A1 .Location in patent: Page/Page column 35.
[2]Patent: CN106883185,2017,A .Location in patent: Paragraph 0017.

17
trifluoroacetamidine [ No CAS ]
[ 105-53-3 ]
[ 672-47-9 ]