[ CAS No. 69034-08-8 ] {[proInfo.proName]}

Name: 69034-08-8|5-(Trifluoromethyl)pyrimidin-2-amine|97%
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SKU: A134395
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Quality Control of [ 69034-08-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 69034-08-8 ]

CAS No. :	69034-08-8	MDL No. :	MFCD10696951
Formula :	C₅H₄F₃N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OUVVCECMELPNNT-UHFFFAOYSA-N
M.W :	163.10	Pubchem ID :	15273574
Synonyms :

Calculated chemistry of [ 69034-08-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	1
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.44
TPSA :	51.8 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) :	-6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.09
Log Po/w (XLOGP3) :	0.74
Log Po/w (WLOGP) :	2.24
Log Po/w (MLOGP) :	0.51
Log Po/w (SILICOS-IT) :	1.25
Consensus Log Po/w :	1.17

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 :	3.61 mg/ml ; 0.0221 mol/l
Class :	Very soluble
Log S (Ali) :	-1.41
Solubility :	6.39 mg/ml ; 0.0392 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.17
Solubility :	1.1 mg/ml ; 0.00676 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.5

Safety of [ 69034-08-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 69034-08-8 ]

* 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 [ 69034-08-8 ]
Downstream synthetic route of [ 69034-08-8 ]

[ 69034-08-8 ] Synthesis Path-Upstream 1~4

1
[ 109-12-6 ]
[ 2314-97-8 ]
[ 69034-08-8 ]

Reference： [1] Journal of Fluorine Chemistry, 2010, vol. 131, # 1, p. 98 - 105
[2] Patent: WO2012/54233, 2012, A1, . Location in patent: Page/Page column 39

2
[ 69034-12-4 ]
[ 69034-08-8 ]

Reference： [1] Patent: CN106588884, 2017, A, . Location in patent: Paragraph 0363; 0364; 0365; 0366

3
[ 3167-50-8 ]
[ 69034-08-8 ]

Reference： [1] Patent: US4248618, 1981, A,

4
[ 50-01-1 ]
[ 176214-18-9 ]
[ 69034-08-8 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 11, p. 1829 - 1832

[ 69034-08-8 ] Synthesis Path-Downstream 1~21

1
[ 50-01-1 ]
[ 176214-18-9 ]
[ 69034-08-8 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 1829 - 1832

2
[ 832692-80-5 ]
[ 69034-08-8 ]
7-(3-methylpyridin-2-yl)-N-(5-(trifluoromethyl)pyrimidin-2-yl)-[1,8]naphthyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 20h;	Heat a mixture of 5-CHLORO-2- (3-METHYLPYRIDIN-2-YL)- [L, 8] NAPHTHYRIDINE (51 mg, 0.2 mmol), <strong>[69034-08-8]2-amino-5-trifluoromethylpyrimidine</strong> (42.0 mg, 0.25 mmol), xantphos (11.6 mg, 0.02 MMOL), Pd2 (dba) 3 (18.3 mg, 0.02 mmol) and CS2C03 (130 mg, 0.4 mmol) in dioxane (2.0 mL) at 100C for 20 hours. Cool the mixture, concentrate under vacuum, dilute with EtOAc/ water (5.0 mL each), filter through celite, wash celite with EtOAc (2 x 5 mL) and dry the combined organic layers with MgSO4. Filter the dried extract and concentrate under vacuum to afford the crude product. Purify by column chromatography using EtOAc as eluent to afford the title. compound. as a yellow SOLID. H NMR (400 MHZ, DMSO-D6) 6 10.92 (s, 1H), 9.0 (m, 3H), 8. 92 (d, 1H, J=1. 8 Hz), 8.58 (d, 1H, J=1.0 Hz), 8. 12 (m, 2H), 7.80 (d, 1H, J=2. 1 HZ), 7. 41 (dd, 1H), 2.65 (s, 3H). MS = 383.3 (M+H).

Reference： [1]Patent: WO2005/7652,2005,A2 .Location in patent: Page/Page column 41; 88-89

3
5-chloro-2-(5-fluoro-3-methylpyridin-2-yl)-1,8-naphthyridine [ No CAS ]
[ 69034-08-8 ]
7-(5-fluoro-3-methylpyridin-2-yl)-N-(5-(trifluoromethyl)pyrimidin-2-yl)-1,8-naphthyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 4h;	3. 7-(5-Fluoro-3-methylpyridin-2-yl)-N-(5-(trifluoromethyl)pyrimidin-2-yl)-l, 8-naphthyridin-4- amine Heat a mixture of 5-chloro-2-(5-fluoro-3-methylpyridin-2-yl)-l,8-naphthyridine (81 mg, 0.3 mmol), <strong>[69034-08-8]2-amino-5-trifluoromethylpyrimidine</strong> (96 mg, 0.6 mmol), xantphos (16.9 mg), Pd2(dba)3 (27.9 mg) and Cs2CO3 (193 mg) in dioxane (2.0 mL) at 1000C for 4 hours. Cool the mixture, concentrate under vacuum, dilute with EtOAc / water (5.0 mL each), filter through celite, wash celite with EtOAc (2 x 5 mL) and dry combined organic layers with MgSO4. Filter the dried extract and concentrate under vacuum to afford crude product. Purify by preparative HPLC to afford title compound as a yellow solid. 1H NMR (400 MHZ, DMSO-D6) delta 10.92 (s, IH), 9.0 (s, 2H), 8.92 (d, IH, J=2.2 Hz), 8.58 (s, IH), 8.17(d, IH, J=Ll Hz), 8.09 (m, IH), 7.8 (d, IH, J=2.4 Hz), 2.69 (s, 3H). MS = 401.31 (M+H). The IC50 determined as described in Example 6 is less than 1 micromolar

Reference： [1]Patent: WO2006/42289,2006,A2 .Location in patent: Page/Page column 49

4
5-chloro-2-(6-methoxy-3-trifluoromethyl-pyridin-2-yl)-[1,8]naphthyridine [ No CAS ]
[ 69034-08-8 ]
[7-(6-methoxy-3-trifluoromethyl-pyridin-2-yl)-[1,8]naphthyridin-4-yl]-(5-trifluoromethyl-pyrimidin-2-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 14h;	C. r7-(6-Methoxy-3-trifluoromethyl-pyridin-2-yl)-r 1 , 8]naphthyridin-4-yl]-(5 -trifluoromethyl- pyrirnidin-2-yl)-amine (compound 6) To a de-gassed mixture of 5-chloro-2-(6-methoxy-3-trifluoromethyl-pyridin-2-yl)- [l,8]naphthyridine (68 mg, 0.2 mmol), cesium carbonate (98 mg, 0.3 mmol), 2-amino-5- trifluoromethyl pyrimidine (37 mg, 0.22 mmol) in dioxane (5 mL) under nitrogen, add Pd2dba3 (12 mg) and xantphos (8 mg). Stir the mixture at 1000C for 14 hours, cool, add water (20 mL) and extract with EtOAc. Dry the combined extracts over Na2SO4, and concentrate under vacuum. Purify by chromatography eluting with DCM/MeOH/ammonium hydroxide mixture to give the title compound. 1H NMR delta (CDCl3) 9.14 (IH, d), 8.81 (2H, s), 8.56 (2H, d), 8.40 (IH, brs), 7.99 (2H, dd), 7.26 (IH, s), 6.92 (IH, d), 4.01 (3H, s). The IC50 determined as described in Example 6 is less than 1 micromolar.

Reference： [1]Patent: WO2006/42289,2006,A2 .Location in patent: Page/Page column 56

5
[ 69034-08-8 ]
2-bromo-5-(trifluoromethyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sodium nitrate; bromine; In water; hydrogen bromide;	(b) 2-Bromo-5-trifluoromethylpyrimidine. The above 2-amino-5-trifluoromethyl pyrimidine (3.6 g) dispersed in aqueous hydrobromic acid (11 ml of 48-50% solution) was treated dropwise with bromine (3.4 g) over a period of about 10 minutes, with stirring, and kept at 0 C. The thick slurry so obtained was kept at 0 C. for another 15 minutes. A solution of sodium nitrate (3.88 g) in water (6 ml) was then added dropwise at 0 C. over a period of 30 minutes. When addition was complete the mixture was stirred for 30 minutes with ice bath cooling and then for 15 minutes at room temperature. The mixture was then poured on to ice (about 150 ml) and made just basic with 2 M sodium hydroxide the mixture was extracted with ether (200 ml) and the ether extracts washed with water, dried (MgSO4) and evaporated to give an oil which solidified on cooling. The solid was extracted with petroleum ether (B.P. 30-40 C.) leaving a gum behind. The petroleum extracts were evaporated to give 2-bromo-5-trifluoromethyl pyrimidine.

Reference： [1]Patent: US4248618,1981,A

6
[ 3167-50-8 ]
[ 69034-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	With HF; SF4;	(a) 2-Amino-5-trifluoromethylpyrimidine. 2-Amino-5-carboxypyrimidine (16.5 g), SF4 (36 g) and HF (100 g) were heated in an autoclave at 120 C. for 8 hours with stirring. The product was washed from the autoclave with water and poured onto ice (about 1.5 liters) and basified with 10 N sodium hydroxide solution. The mixture was filtered and the filter cake dried, powdered, and extracted with ether (2*400 ml). The ether extracts gave 2-amino-5-trifluoromethyl pyrimidine (9 g).

Reference： [1]Patent: US4248618,1981,A

7
[ 109-12-6 ]
[ 2314-97-8 ]
[ 69034-08-8 ]

Yield	Reaction Conditions	Operation in experiment
		SYNTHESIS EXAMPLE 2Preparation of N-[[2-chloro-5-(trifluoromethyl)phenyl]sulfonyl]-6- (trifluoromethyl)imidazo[ 1 ,2-a]pyrimidine-2-carboxamide (compound 6) Step A: Preparation of 2-amino-5-(trifluoromethyl)pyrimidineA 2-L flask fitted with a dry ice condenser and addition funnel was charged with dimethylsulfoxide (500 mL) and a 0.5 M solution of sulfuric acid in dimethylsulfoxide (400 mL), followed by the addition of 2-aminopyrimidine (20.0 g, 21 1 mmol). The reaction mixture was stirred vigorously for 5 minutes, and then a 1 M solution of iron(II) sulfate in water (60 mL) was added. Trifluoromethyl iodide (200 g, 1.02 moles) was added below the surface of the reaction mixture at room temperature. The reaction mixture was then cooled to 0 C, and 50% aqueous hydrogen peroxide (20 mL, 294 mmol) was added dropwise over one hour. The ice bath was then removed, and the reaction mixture was allowed to warm to room temperature over three hours. The reaction mixture was then carefully neutralized to pH 6.5 with aqueous sodium carbonate. The reaction mixture was then extracted with ethyl acetate (3 x 300 mL), and the combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure. The resulting oil was purified by chromatography on silica gel eluting with a hexane/ethyl acetate gradient to afford 4.51 g of the title compound as an off white solid. 1H NMR (CDCI3) delta 8.51 (s, 2H), 5.55 (br s, 2H).

Reference： [1]Journal of Fluorine Chemistry,2010,vol. 131,p. 98 - 105
[2]Patent: WO2012/54233,2012,A1 .Location in patent: Page/Page column 39

8
[ 1220632-30-3 ]
[ 69034-08-8 ]
7-[3-(trifluoromethyl)pyridin-2-yl]-N-[5-(trifluoromethyl)pyrimidin-2-yl]-1,8-naphthyridin-4-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4359 - 4363

9
C₁₃⁽¹⁴⁾CH₇ClF₃N₃ [ No CAS ]
[ 69034-08-8 ]
[ 1245523-04-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4359 - 4363

10
[ 1113-59-3 ]
[ 69034-08-8 ]
[ 1372197-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; for 24h;Reflux;	Step B : Preparation of the HBr salt of 6-(trifluoromethyl)imidazo[ 1 ,2-a]pyrimidine-2- carboxylic acidThe product of Step A (1.0 g, 6.1 mmol) was added to a solution of bromopyruvic acid (1.025 g, 6.134 mmol) in dioxane (30 mL), and the reaction mixture was heated at reflux for 24 hours. The dioxane was removed under reduced pressure to give 798 mg of the title compound. .H NMR ((CD3)2SO) delta 9.67 (s, 1H), 8.99 (s, 1H), 8.49 (s, 1H), 5.98 (br s, 2H).

Reference： [1]Patent: WO2012/54233,2012,A1 .Location in patent: Page/Page column 39

11
[ 1131220-37-5 ]
[ 69034-08-8 ]
[ 1400995-12-1 ]

Reference： [1]Patent: US2012/245172,2012,A1
[2]Patent: WO2012/126922,2012,A1

12
[ 1131220-37-5 ]
[ 69034-08-8 ]
[ 1400997-18-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 120℃; for 16h;Inert atmosphere;	EXAMPLE 19((S)-4-Morpholin-2-yl-phenyl)-(5-trifluoromethyl-pyrimidin-2-yl)-aminea) (S)-2-[4-(5-Trifluoromethyl-pyrimidin-2-ylamino)-phenyl]-morpholine-4-carboxylic acid tert-butyl esterTo a 10 ml glass vial was added (S)-2-(4-bromo-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (70 mg, CAS 1131220-37-5) and <strong>[69034-08-8]5-trifluoromethyl-pyrimidin-2-ylamine</strong> (66.7 mg, CAS 69034-08-8) in dioxane (2 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (14.3 mg), tris(dibenzylideneacetone)dipalladium(0) (7.49 mg) and sodium tert-butoxide (21.6 mg) were then added. The vial was capped and heated at 120 C. for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in hexanes) to afford (S)-2-[4-(5-trifluoromethyl-pyrimidin-2-ylamino)-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (94 mg, quant.) as an off-white solid. MS (ISP): 425.2 ([M+H]+).
100%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 120℃; for 16h;Inert atmosphere; capped vial;	To a 10 ml glass vial was added (S)-2-(4-bromo-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (70 mg, CAS 1131220-37-5) and <strong>[69034-08-8]5-trifluoromethyl-pyrimidin-2-ylamine</strong> (66.7 mg, CAS 69034-08-8) in dioxane (2 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert- butylphosphino-2',4',6'-triisopropylbiphenyl (14.3 mg), tris(dibenzylideneacetone)dipalladium(0) (7.49 mg) and sodium tert-butoxide (21.6 mg) were then added. The vial was capped and heated at 120 C for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in hexanes) to afford (S)-2-[4-(5-trifluoromethyl-pyrimidin-2- ylamino)-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (94 mg, quant.) as an off-white solid. MS (ISP): 425.2 ([M+H]+).

Reference： [1]Patent: US2012/245172,2012,A1 .Location in patent: Page/Page column 32
[2]Patent: WO2012/126922,2012,A1 .Location in patent: Page/Page column 56

13
[ 1400997-38-7 ]
[ 69034-08-8 ]
[ 1400997-56-9 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 120℃; for 16h;Inert atmosphere;	EXAMPLE 121(RS)-(2-Fluoro-4-morpholin-2-yl-phenyl)-(5-trifluoromethyl-pyrimidin-2-yl)-aminea) (RS)-2-[3-Fluoro-4-(5-trifluoromethyl-pyrimidin-2-ylamino)-phenyl]-morpholine-4-carboxylic acid tert-butyl esterTo a 20 ml glass vial was added (RS)-2-(4-bromo-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (200 mg, example 96(e)) and <strong>[69034-08-8]5-trifluoromethyl-pyrimidin-2-ylamine</strong> (145 mg, CAS 69034-08-8) in dioxane (5 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (38.9 mg), tris(dibenzylideneacetone)dipalladium(0) (20.3 mg) and sodium tert-butoxide (59.9 mg) were then added. The vial was capped and heated at 120 C. for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in heptane) to afford (RS)-2-[3-fluoro-4-(5-trifluoromethyl-pyrimidin-2-ylamino)-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (115 mg, 47%) as a yellow gum. MS (ISP): 441.4 ([M-H]-).
47%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 120℃; for 16h;Inert atmosphere; capped vial;	To a 20 ml glass vial was added (RS)-2-(4-bromo-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (200 mg, example 96(e)) and <strong>[69034-08-8]5-trifluoromethyl-pyrimidin-2-ylamine</strong> (145 mg, CAS 69034-08-8) in dioxane (5 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (38.9 mg),tris(dibenzylideneacetone)dipalladium(0) (20.3 mg) and sodium tert-butoxide (59.9 mg) were then added. The vial was capped and heated at 120 C for 16 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 50% EtOAc in heptane) to afford (RS)-2-[3-fluoro-4-(5-trifluoromethyl-pyrimidin-2-ylamino)-phenyl]-morpholine-4- carboxylic acid tert-butyl ester (115 mg, 47%) as a yellow gum. MS (ISP): 441.4 ([M-H]").

Reference： [1]Patent: US2012/245172,2012,A1 .Location in patent: Page/Page column 57-58
[2]Patent: WO2012/126922,2012,A1 .Location in patent: Page/Page column 103; 104

14
[ 1400997-81-0 ]
[ 69034-08-8 ]
[ 1400997-85-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere;	EXAMPLE 196(R)-N-(3-Fluoro-4-(morpholin-2-yl)phenyl)-<strong>[69034-08-8]5-(trifluoromethyl)pyrimidin-2-amine</strong>a) (R)-tert-Butyl 2-(2-fluoro-4-(5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)morpholine-4-carboxylateTo a 25 ml glass vial was added (+)-(R)-tert-butyl 2-(4-bromo-2-fluorophenyl)morpholine-4-carboxylate (300 mg, example 192(f)) and <strong>[69034-08-8]5-trifluoromethyl-pyrimidin-2-ylamine</strong> (156 mg, CAS 69034-08-8) in dioxane (5 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (58.3 mg), tris(dibenzylideneacetone)dipalladium(0) (30.5 mg) and sodium tert-butoxide (89.8 mg) were then added. The vial was capped and heated at 100 C. for 2 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in heptane) to afford (R)-tert-butyl 2-(2-fluoro-4-(5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)morpholine-4-carboxylate (304 mg, 83%) as an amorphous yellow solid. MS (ISP): 441.2 ([M-H]-).
83%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere; capped vial;	To a 25 ml glass vial was added (+)-(R)-tert-butyl 2-(4-bromo-2-fluorophenyl)morpholine-4- carboxylate (300 mg, example 192(f)) and <strong>[69034-08-8]5-trifluoromethyl-pyrimidin-2-ylamine</strong> (156 mg, CAS 69034-08-8) in dioxane (5 ml). The reaction mixture was purged with argon for 5 min. 2-Di-tert- butylphosphino-2',4',6'-triisopropylbiphenyl (58.3 mg), tris(dibenzylideneacetone)dipalladium(0) (30.5 mg) and sodium tert-butoxide (89.8 mg) were then added. The vial was capped and heated at 100 C for 2 h. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in heptane) to afford (R)-tert-butyl 2-(2-fluoro-4-(5- (trifluoromethyl)pyrimidin-2-ylamino)phenyl)morpholine-4-carboxylate (304 mg, 83%) as an amorphous yellow solid. MS (ISP): 441.2 ([M-H]").

Reference： [1]Patent: US2012/245172,2012,A1 .Location in patent: Page/Page column 76-77
[2]Patent: WO2012/126922,2012,A1 .Location in patent: Page/Page column 138; 139

15
[ 69034-12-4 ]
[ 69034-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In 1-methyl-pyrrolidin-2-one; at 120℃; for 24h;	Compound 2-46 (225 mg, 1.23 mmol) was placed in a sealed tube, aqueous ammonia (10 mL) and N-methylpyrrolidone (10 mL) were added and stirred at 120 C for 24 h. Cooled to room temperature, and the solvent was recovered under reduced pressure to give a residue. Purification by silica gel column chromatography using PE: EtOAc (2: 1) as eluent gave a white solid.
	With ammonia; In ethanol; at 20℃; for 2h;	The compound 2-chloro-5-trifluoromethylpyrimidine (910 mg, 5 mmol) was dissolved in ethanol (5 mL) solution, and an ammonia-saturated ethanol solution (15 mL) was added dropwise under ice bath, reacted at room temperature for 2 h, and recovered under reduced pressure The residue obtained from the solvent was purified by silica gel column chromatography using PE:EA (4:1) as the eluent to obtain a white solid.

Reference： [1]Patent: CN106588884,2017,A .Location in patent: Paragraph 0363; 0364; 0365; 0366
[2]Patent: CN111253370,2020,A .Location in patent: Paragraph 0081-0083

16
[ 16173-52-7 ]
[ 69034-08-8 ]
4-formyl-N-(5-(trifluoromethyl)pyrimidin-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		To a suspension of 4-formylbenzoic acid (580 mg, 3.86 mmol) in DCM (20 mL) were added oxalyl chloride (0.46 mL, 5.4 mmol) and catalytic DMF. The reaction mixture was stirred at 23C for 3 h. Then the mixture was concentrated in vacuo, and the crude residue was azeotroped with toluene (2X) to give crude 4-formylbenzoylchloride which was used directly as described below. To a solution of 2-amino-5- trifluoromethylpyrimidine (1.26 g, 7.73 mmol) in THF 30 mL was added NaH (60% dispersion in mineral oil, 340 mg, 8.49 mmol). The mixture was stirred at 23C for 30 min. To this mixture was added 4-formylbenzoylchloride (prepared as described above) as a solution in THF (15 mL). The reaction mixture was stirred at 23C for 3.5 h. The mixture was then quenched with saturated NH4Cl (aq) (20 mL), and extracted with EtOAc (3X50 mL).The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by FCC (SiO2, elution with 0-30% EtOAc/hexanes) to provide 407 mg (36%) of Intermediate III.14.1H NMR (400 MHz, CDCl3) dppm 10.14 (s, 1H), 8.93 (s, 2H), 8.84 (br s, 1H), 8.12 (d, 2H), 8.05 (d, 2H).

Reference： [1]Patent: WO2017/214359,2017,A1 .Location in patent: Page/Page column 89

17
2-bromo-1-[3-methyl-6-(trifluoromethyl)-3H-imidazo [4,5-b]pyridin-2-yl]ethan-1-one [ No CAS ]
[ 69034-08-8 ]
3-methyl-6-(trifluoromethyl)-2-[6-(trifluoromethyl)imidazo[1,2-a]pyrimidin-2-yl]-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
445 mg	In acetonitrile; for 7.5h;Reflux;	11050] 250 mg of <strong>[69034-08-8]5-(trifluoromethyl)pyrimidin-2-amine</strong> was dissolved in 10 ml of acetonitrile, and 550 mg of 2-bromo-1 -[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5- b]pyridin-2-yl]ethanone was added at room temperature. Afier the addition, the reaction mixture was stirred under reflux with heating for 7.5 hours. Afier the reaction, 10 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration to obtain 445 mg of the desired product as a yellow solid.11051] Melting point: 283-285 C.11052] ?H-NMR (CDC13): oe8.92-8.89 (m, 1H), 8.84 (d, J=2.4 Hz, 1H), 8.73 (s, 1H), 8.57 (s, 1H), 8.29 (s, 1H), 4.53 (s, 3H).

Reference： [1]Patent: US2018/22760,2018,A1 .Location in patent: Paragraph 1050; 1051; 1052
[2]Patent: JP2020/111539,2020,A .Location in patent: Paragraph 0593-0594

18
[ 1113-59-3 ]
[ 69034-08-8 ]
[ 1372197-47-1 ]
C₈H₄F₃N₃O₂*BrH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; at 100℃; for 16h;	To a stirred solution of <strong>[69034-08-8]5-(trifluoromethyl)pyrimidin-2-amine</strong>(A36, 4.5 g, 27.60 mmol) in l,4-dioxane(80 mL) was added 3-bromo-2-oxopropanoic acid(A15, 6.87 g , 41.4 mmol .The reaction mixture was heated at 100 C for 16 h. After completion of reaction mixture was concentrated under reduced pressure. The crude product was triturated with ethyl acetate and dried to afford 6-(trifluoromethyl)imidazo[l,2-a]pyrimidine-2-carboxylic acid A37 and A38 as dark brown mixture Yield: 7.0 g,(crude). LC-MS m/z : 229.96[M-H]

Reference： [1]Patent: WO2019/102494,2019,A1 .Location in patent: Paragraph 000187

19
[ 67-56-1 ]
[ 1113-59-3 ]
[ 69034-08-8 ]
methyl 6-(trifluoromethyl)imidazo[1,2-a]pyrimidine-2-carboxylate [ No CAS ]
C₉H₆F₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of the mixture A37 and A38(3, 4.5 g, l9.4mmol) in methanol(100 mL) was added drop wise H2S04(10 mL) and the reaction mixture was stirred at 80 C temperature for l6h. After completion of reaction organic solvent was evaporated and the aqueous layer was basified with Sat.NaHCCL up to pH 8 to 9 and aqueous layer was extracted with 10% MeOH in DCM and then concentrated under reduced pressure. The obtained crude was purified by column chromatography using 10% methanol in dichloromethane as eluent to afford methyl 6-(trifluoromethyl)imidazo[l,2- a]pyrimidine-2-carboxylate 1-57 and 1-58 as pink solid Yield: 0.5 g,(10%). LC-MS m/z : 245.97[M+H]+.

Reference： [1]Patent: WO2019/102494,2019,A1 .Location in patent: Paragraph 000188

20
3-(4-tert-butoxycarbonylaminocyclohexylamino)-5-bromo-2-cyanopyridine [ No CAS ]
[ 69034-08-8 ]
C₁₇H₁₈F₃N₇ [ No CAS ]

Reference： [1]Patent: CN111253370,2020,A

21
3-(4-tert-butoxycarbonylaminocyclohexylamino)-5-bromo-2-cyanopyridine [ No CAS ]
[ 69034-08-8 ]
C₂₂H₂₆F₃N₇O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 5h;Inert atmosphere; Reflux;	Under nitrogen protection, to intermediate 1-9 (90.0mg, 0.55mmol), intermediate 1-10 (250.0mg, 0.63mmol), tetratriphenylphosphine palladium (31.0mg, 0.027mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (31.0mg, 0.055mmol), a mixture of cesium carbonate (268.0 mg, 0.82 mmol) was added to anhydrous dioxane (10 mL), stirred under reflux for 5 h, filtered with suction, and the solvent was recovered under reduced pressure to obtain a residue. Purified by silica gel column chromatography, using PE:EA (1:1) as eluent to obtain a white solid. Deprotection with ethyl acetate saturated with hydrochloric acid gave compound 25 as a white solid. Yield: 60%.

Reference： [1]Patent: CN111253370,2020,A .Location in patent: Paragraph 0081; 0086-0087

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
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P263	Avoid contact during pregnancy/while nursing.
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
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P307	IF exposed:
P308	IF exposed or concerned:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
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P315	Get immediate medical advice/attention.
P320
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P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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. 69034-08-8 ] {[proInfo.proName]}

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[ 69034-08-8 ] Synthesis Path-Upstream 1~4

[ 69034-08-8 ] Synthesis Path-Downstream 1~21

Related Functional Groups of [ 69034-08-8 ]

Fluorinated Building Blocks

Amines

Trifluoromethyls

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Pyrimidines

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[ 69034-08-8 ]

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[ 69034-08-8 ]