[ CAS No. 3029-64-9 ] {[proInfo.proName]}

Name: 3029-64-9|2,4,6-Trichloro-5-cyanopyrimidine|98%
Brand: Ambeed
SKU: A425559
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Quality Control of [ 3029-64-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 3029-64-9 ]

CAS No. :	3029-64-9	MDL No. :	MFCD07636745
Formula :	C₅Cl₃N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IAJCAZVXGKGAQK-UHFFFAOYSA-N
M.W :	208.43	Pubchem ID :	250945
Synonyms :

Calculated chemistry of [ 3029-64-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.78
TPSA :	49.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	2.81
Log Po/w (WLOGP) :	2.31
Log Po/w (MLOGP) :	0.79
Log Po/w (SILICOS-IT) :	2.87
Consensus Log Po/w :	2.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.31
Solubility :	0.103 mg/ml ; 0.000494 mol/l
Class :	Soluble
Log S (Ali) :	-3.51
Solubility :	0.0647 mg/ml ; 0.00031 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.59
Solubility :	0.0532 mg/ml ; 0.000255 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 3029-64-9 ]

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

Application In Synthesis of [ 3029-64-9 ]

* 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 [ 3029-64-9 ]
Downstream synthetic route of [ 3029-64-9 ]

[ 3029-64-9 ] Synthesis Path-Upstream 1~1

1
[ 857200-56-7 ]
[ 3029-64-9 ]

Reference： [1] Patent: US4092150, 1978, A,

[ 3029-64-9 ] Synthesis Path-Downstream 1~81

3
[ 3029-64-9 ]
[ 108-44-1 ]
C₁₂H₈Cl₂N₄ [ No CAS ]

Reference： [1]Patent: EP1184376,2002,A1 .Location in patent: Page 13

4
[ 3029-64-9 ]
[ 591-19-5 ]
C₁₁H₅BrCl₂N₄ [ No CAS ]

Reference： [1]Patent: EP1184376,2002,A1 .Location in patent: Page 13

5
[ 3029-64-9 ]
[ 7087-68-5 ]
[ 765-30-0 ]
[ 66309-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane;	b 4-Chloro-2,6-bis-cyclopropylamino-pyrimidine-5-carbonitrile To a solution of 500 mg (2.4 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyano-pyrimidine</strong> in 30 ml of dioxane were added at room temperature 0.84 ml (4.8 mmol) of N-ethyl-diisopropylamine and 0.52 ml (7.2 mmol) of cyclopropylamine. The yellow reaction mixture was stirred at room temperature during 18 hours, then, for working-up, it was evaporated under reduced pressure. The residue obtained was then chromatographed on silica gel using a 3:1 mixture of dichloromethane and hexane as the eluent yielding 328 mg (1.3 mmol, 55percent of theory) of 4-chloro-2,6-bis-cyclopropylamino-pyrimidine-5-carbonitrile as a yellow solid; MS: [M+H]+=249.

Reference： [1]Patent: US2003/60466,2003,A1

6
[ 141-43-5 ]
[ 3029-64-9 ]
[ 7087-68-5 ]
[ 478180-25-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; ethanol; dichloromethane;	a 4-Chloro-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile A solution of 10.0 g (48 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyano-pyrimidine</strong> in 150 ml of dioxane was treated at 0° C. with 16.4 ml (96 mmol) of N-ethyl-diisopropylamine, followed by 8.7 ml (144 mmol) of ethanolamine. While warming up to room temperature, yellowish solid material started to precipitate. The yellow solution was stirred overnight, then the resulting material was separated by filtration and the mother liquor evaporated to dryness. The residue was stirred with dichloromethane and the solid filtered. To eliminate the ethanolammonium chloride, the two combined solid fractions were treated with 100 ml of ethanol, thereupon the resulting product was washed with 150 ml of dichloromethane. After drying under reduced pressure, 10.45 g (40.6 mmol, 84.5 of theory) of 4-chloro-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile were obtained as a yellowish powder.

Reference： [1]Patent: US2003/60466,2003,A1

7
(E/Z)-2,4,6-trichloro-pyrimidine-5-carbaldehyde oxime [ No CAS ]
[ 3029-64-9 ]

Yield	Reaction Conditions	Operation in experiment
	In thionyl chloride;	(iii) 2,4,6-Trichloro-5-cyano-pyrimidine A solution of 8.03 g (0.035 mol) of (E/Z)-2,4,6-trichloro-pyrimidine-5-carbaldehyde oxime in 85 ml of thionylchloride prepared at 0° C., was heated to room temperature, then, during 2 hours to reflux. For the working-up, the yellow reaction mixture was cooled to room temperature, then evaporated under reduced pressure to yield 7.57 g of crude 2,4,6-trichloro-5-cyano-pyrimidine as a yellow-brownish solid. For purification, the crude material was chromatographed on silica gel using a 5:1 mixture of cyclohexane and dichloromethane as the eluent giving 4.38 g (0.021 mol, 59percent of theory) of 2,4,6-trichloro-5-cyano-pyrimidine as a white solid; MS: [M]+=207.

Reference： [1]Patent: US2003/60466,2003,A1

Yield	Reaction Conditions	Operation in experiment
65%		EXAMPLE T 5-Cyano-2,4,6-trichloro-pyrimidine Prepared [see C.A. 62, 7775 (1965)] from 5-carbamoyl-2,4,6-trihydroxy-pyrimidine, phosphorus oxychloride and dimethyl aniline (18 hours, 100°C). M.p. 123°C (petroleum ether b.p.: 100°-140°C); yield: 65percent of theory. 5-Cyano-4,6-dichloro-2-methylthio-pyrimidine was prepared in analogous manner from 5-carbamoyl-4,6-dihydroxy-2-methylthiopyrimidine and phosphorus oxychloride/diethyl aniline (4 hours, reflux). M.p. 107°C (petroleum ether).

9
[ 123-90-0 ]
[ 3029-64-9 ]
[ 56032-13-4 ]

Yield	Reaction Conditions	Operation in experiment
4.5%		5-Cyano-4,6 -dichloro-2-thiomorpholino-pyrimidine (m.p. 99°C, yield: 4.5percent of theory) from 5-cyano-2,4,6 -trichloro-pyrimidine and thiomorpholine.

Reference： [1]Patent: US3975384,1976,A

10
[ 3029-64-9 ]
[ 56032-15-6 ]

Yield	Reaction Conditions	Operation in experiment
10%	In methanol;	5-Cyano-4,6 -dichloro-2-methoxy-pyrimidine (m.p. 156°C, yield: 10percent of theory) from 5-cyano-2,4,6-trichloro-pyrimidine and methanol (reaction time: 20 hours; reaction temperature: 65°C; without potassium carbonate).

Reference： [1]Patent: US3975384,1976,A

11
[ 3029-64-9 ]
[ 109-89-7 ]
[ 66309-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; water;	EXAMPLE VIII 4,6-Dichloro-2-diethylamino-5-pyrimidinecarbonitrile A stirred solution of 6.3 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 150 ml of diethyl ether was cooled to -10°, and a solution of 4.4 grams of diethylamine in 75 ml of diethyl ether was added dropwise. Upon complete addition, the reaction mixture was stirred at -10° for 1 hour. Water was added to the reaction mixture. The diethyl ether layer was separated and dried over magnesium sulfate. The mixture was filtered, and the filtrate was evaporated under reduced pressure to a residue. The residue was recrystallized from methylcyclohexane to give 3.8 grams of 4,6-dichloro-2-diethylamino-5-pyrimidinecarbonitrile; mp, 125°-126°. Analysis: Calculated for C9 H10 Cl2 N4: C,44.10; H,4.07; N,22.85; Found: C,44.l3; H,4.28; N,23.14.

Reference： [1]Patent: US4092150,1978,A

12
[ 3029-64-9 ]
[ 109-89-7 ]
[ 66309-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether;	EXAMPLE XV 4-Chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile To a stirred solution of 6.3 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 150 ml of diethyl ether at 10° was added dropwise 8.8 grams of diethylamine in 150 ml of diethyl ether. Upon complete addition, the reaction mixture was allowed to warm to room temperature, where it was stirred for 16 hours. The reaction mixture was heated under reflux for 1 hour, then cooled to room temperature. The reaction mixture was washed with water, and the diethyl ether layer was separated. The aqueous layer was washed with diethyl ether. The ether layers were combined and dried over magnesium sulfate. The mixture was filtered, and the filtrate was evaporated under reduced pressure to a residue. The residue was recrystallized from petroleum ether to give crude 4-chloro-2,6-bis(diethylamino)-5-pyrimidinecarbonitrile.

Reference： [1]Patent: US4092150,1978,A

13
[ 75-04-7 ]
[ 3029-64-9 ]
[ 66308-99-4 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrachloromethane; diethyl ether; water; acetone;	EXAMPLE V 4,6-Dichloro-2-ethylamino-5-pyrimidinecarbonitrile A stirred solution of 12.9 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 150 ml of acetone was cooled to -10°, and 7.7 grams of an aqueous 70percent ethylamine solution was added dropwise during 2 hours. The temperature of the reaction mixture was maintained at -10° throughout the addition. Following complete addition, the reaction mixture was allowed to warm to room temperature, where it stood for 16 hours. Then most of the acetone was removed by evaporation under reduced pressure. The residue was extracted with a mixture of water and diethyl ether. The ether layer was separated and dried over magnesium sulfate. The dried ether layer was filtered, and the ether was removed under reduced pressure. The residue was recrystallized from a mixture of methylcyclohexane and benzene, then from carbon tetrachloride, to give 4.2 grams of 4,6-dichloro-2-ethylamino-5-pyrimidinecarbonitrile; mp, 145-150°. Analysis: Calculated for C7 H6 Cl2 H4: C,38.74; H,2.78; N,25.80; Found: C,38.47; H,2.97; N,25.90.

Reference： [1]Patent: US4092150,1978,A

14
[ 3029-64-9 ]
[ 75-31-0 ]
[ 66308-92-7 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; water;	EXAMPLE VI 4,6-Dichloro-2-isopropylamino-5-pyrimidinecarbonitrile A stirred solution of 4.2 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 100 ml of diethyl ether was cooled to between -5° and -10°, and a solution of 2.4 grams of isopropylamine in 100 ml of diethyl ether was added dropwise. Upon complete addition, water was added to the reaction mixture, and the ether layer was separated. The ethereal layer was dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure. The residue was recrystallized from methylcyclohexane to give 2.4 grams of 4,6-dichloro-2-isopropylamino-5-pyrimidinecarbonitrile; mp, 179°-181°. Analysis: Calculated for C8 H8 Cl2 N4: C,41.57; H,3.47; N,24.23; Found: C,41.33; H,3.35; N,23.97.

Reference： [1]Patent: US4092150,1978,A

15
[ 3029-64-9 ]
[ 19355-69-2 ]
[ 66308-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; acetone;	EXAMPLE IV 4,6-Dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile A stirred solution of 6.3 grams of <strong>[3029-64-9]2,4,6-trichloro-5-pyrimidinecarbonitrile</strong> in 25 ml of acetone was cooled to -10°, and 2.5 grams of 2-amino-2-methylpropionitrile was added. With the reaction mixture at -10°, a solution of 1.3 grams of sodium hydroxide in 3.5 ml of water was added dropwise. Upon complete addition, the reaction mixture was stirred at -10° for 30 minutes. The acetone was removed under reduced pressure; the residue was extracted with diethyl ether, and the extract was separated and dried over magnesium sulfate. The extract was filtered, and the filtrate was evaporated under reduced pressure, yielding a residue. The residue was recrystallized from methylcyclohexane to give 3.1 grams of 4,6-dichloro-2-(1-cyano-1-methylethylamino)-5-pyrimidinecarbonitrile; mp, 154-158°. Analysis: Calculated for C9 H7 Cl2 N5: C,42.21; H,2.73; N,27.34; Found: C,42.26; H,2.92; N,27.35.

Reference： [1]Patent: US4092150,1978,A

16
[ 857200-56-7 ]
[ 3029-64-9 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate;	EXAMPLE II 2,4,6-Trichloro-5-pyrimidinecarbonitrile A stirred mixture of 40 grams (24 ml) of phosphorus oxychloride and 9 grams of 2,4,6-trihydroxy-5-pyrimidinecarboxamide was refluxed for 1 hour. An additional 12 ml of phosphorus oxychloride was then added, and the mixture was refluxed for an additional 3 hours. The excess phosphorus oxychloride was removed by distillation, and the residue was poured into a mixture of ice and water. The aqueous mixture was extracted with chloroform. The extract was dried with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to a residue. The residue was sublimed to give 2 grams of 2,4,6-trichloro-5-pyrimidinecarbonitrile; mp, 117°-119°. The mass spectrum of the product was consistent with the assigned structure.

Reference： [1]Patent: US4092150,1978,A

17
[ 3029-64-9 ]
[ 10272-07-8 ]
[ 725238-05-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7347 - 7357

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[ 3029-64-9 ]
[ 900456-21-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With ammonia; In 1,4-dioxane; at 20 - 80℃;	PREPARATION 982,4-Diamino-6-chloropyrimidine-5-carbonitrileA mixture of <strong>[3029-64-9]2,4,6-trichloropyrimidine-5-carbonitrile</strong> (200mg, 0.96 mmol) and a 0.5M solution of NH3 in dioxane (12ml, 6 mmol) and the mixture stirred at room temperature for 2h. The monosubstituted intermediate was obtained and 10 ml more of NH3 in dioxane were added and the mixture stirred at 80C over the weekend. A suspension was obtained, the solid filtered off and the filtrate concentrated to give a solid which was triturated in diethyl ether. The title compound was obtained as a beige solid (156mg, 78% yield).LRMS (m/z): 170 (M+1 )+.
51%	With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 1h;	Step 3. 2,4-diamino-6- chloropyrimidin-5-formonitrile ; <strong>[3029-64-9]2,4,6-trichloropyrimidin-5-formonitrile</strong> (9 g, 43.5 mmol), dioxane (40 mL), and ammonium hydroxide (36%, 40 mL) were added to a 150-mL round-bottom flask, and heated to 50 C. to react for 1 hour. After the completion of the reaction, the resultant mixture was cooled to room temperature, followed by an addition of 50 mL of ice water, and then placed and cooled in an ice-bath and stirred for 1.5 hours. The resultant mixture was filtered to obtain a filter residue. The filter residue was washed with H2O to obtain a light yellow solid of 3.8 g. The yield was 51%. LCMS (ESI): m/z=170 (M+H)+.
4.5 g	With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 3h;	Ammonium hydroxide (20 mL) was added to a solution of <strong>[3029-64-9]2,4,6-trichloropyrimidine-5-carbonitrile</strong> (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50 C. and stirred for 3 hrs. The reaction mixture was cooled to 10 C. and water (50 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford the compound depicted above as a white solid (4.5 g) 13H NMR (100 MHz, DMSO) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS m/z=169.9 (M+H)+.

4.5 g	With ammonium hydroxide; In 1,4-dioxane; water; at 10 - 50℃; for 3h;	(2,4-diamino-6-chloropyrimidine-5-carbonitrile) Ammonium hydroxide (20 mL) was added to a solution of <strong>[3029-64-9]2,4,6-trichloropyrimidine-5-carbonitrile</strong> (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50 C. and stirred for 3 hrs. The reaction mixture was cooled to 10 C. and water (50 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to obtain the title compound as a white solid (4.5 g) 13H NMR (100 MHz, DMSO) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS m/z=169.9 (M+H)+.
	With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 3h;	10624] Ammonium hydroxide (20 mE) was added to a solution of 2,4,6-trichioropyrimidine-5-carbonitrile (5.0 g, 24 mmol) in dioxane (20 mE) at room temperature. The solution was heated to 50 C. and stirred for 3 hrs. The reaction mixture was cooled to 10C. and added to water (50 mE). The resulting solid was filtered, washed with water, and dried under high vacuum to afford the title compound. 13R NMR(100 MHz, DM50) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS mlz=1 69.9 (M+H+).
	With ammonium hydroxide; In 1,4-dioxane; at 10 - 50℃; for 3h;	Ammonium hydroxide (20 mL) was added to a solution of 2 ,4,6-tric&oropyrimidine- 5-carbonitrile (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50C and stirred for 3 hrs. The reaction mixture was cooled to 10C and water (50 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford the title compound as a white solid. 13C NMR (100 MHz, DMSO) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS m/z - 169.9 (M+H)+.
	With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 3h;	Ammonium hydroxide (20 mL) was added to a solution of <strong>[3029-64-9]2,4,6-trichloropyrimidine-5-carbonitrile</strong> (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50 C. and stirred for 3 hours. The reaction mixture was cooled to 10 C. and water (50 mL) added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford 2,4-diamino-6-chloropyrimidine-5-carbonitrile. 13H NMR (100 MHz, DMSO) 164.8, 162.6, 161.9, 115.8, 77.6. ES/MS m/z=169.9 (M+H+).
	With ammonium hydroxide; In 1,4-dioxane; at 20 - 50℃; for 3h;	Example 3, Preparation of a Compound of Formula (3) A. Preparation of a Compound of Formula (3) in which R4 is CN, R6 and R7 are N, and X is CI (2,4-diammo-6^chloiopyr^ Ammonium hydroxide (20 mL) was added to a solution of 2,4,6- trichloropyriniidine-5-carbonitrile (5.0 g, 24 mmol) in dioxane (20 mL) at room temperature. The solution was warmed to 50C and stirred for 3 hrs. The reaction mixture was cooled to 10C and water (50 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford the above compound. 13H NMR (100 MHz, DMSO) 64.8, 162.6, 161.9, 115.8, 77.6. ES MS mh = 169.9 (M+H)
0.8 g	With ammonium hydroxide; In 1,4-dioxane; at 50℃; for 3h;	Ammonium hydroxide (4 mL) was added to a solution of 2,4,6-trichloropyrimidine-5- carbonitrile (1.0 g, 4.8 mmol) in dioxane (4 mL) at room temperature. The solution was warmed to 50C and stirred for 3 hrs. The reaction mixture was cooled to 10C and water (10 mL) was added. The resulting solid was filtered, washed with water, and dried under high vacuum to afford 2,4,6-triamino-pyrimidine-5 carbonitrile as a white solid (0.8 g). Mass Spectrum (ESI) m/e: 170 (M+H).

Reference： [1]Patent: WO2012/146666,2012,A1 .Location in patent: Page/Page column 166
[2]Patent: US2019/255057,2019,A1 .Location in patent: Paragraph 0086; 0089
[3]Patent: US2014/179718,2014,A1 .Location in patent: Paragraph 0667
[4]Patent: US2014/371246,2014,A1 .Location in patent: Paragraph 0631; 0632
[5]Patent: US2015/361095,2015,A1 .Location in patent: Paragraph 0623; 0624
[6]Patent: WO2015/191754,2015,A2 .Location in patent: Paragraph 00164
[7]Patent: US2015/361070,2015,A1 .Location in patent: Paragraph 0274
[8]Patent: WO2015/200352,2015,A1 .Location in patent: Paragraph 00233; 00234; 00235
[9]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548
[10]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242
[11]Journal of Medicinal Chemistry,2017,vol. 60,p. 1555 - 1567
[12]Patent: WO2017/155741,2017,A1 .Location in patent: Paragraph 081; 082

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[ 1615251-72-3 ]

Reference： [1]Patent: US2014/179718,2014,A1
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

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(S)-2,4-diamino-6-((5-chloro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)(cyclopropyl)methylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

21
[ 3029-64-9 ]
(S)-2,4-diamino-6-((1-(5-chloro-4-oxo-3-(1H-pyrazol-3-yl)-3,4-dihydroquinazolin-2-yl)propyl)amino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Patent: US2015/361070,2015,A1

22
[ 3029-64-9 ]
2,4-diamino-6-((cyclopropyl(5-fluoro-3-(3-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)methyl)amino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/200352,2015,A1

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[ 3029-64-9 ]
[ 1615253-03-6 ]

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[ 1615251-99-4 ]

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[ 1615251-81-4 ]

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[ 3029-64-9 ]
[ 1615251-82-5 ]

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[ 1615251-87-0 ]

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(S)-2,4-diamino-6-((1-(3-(3,5-difluorophenyl)-8-iodo-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl)amino)-pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

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[ 3029-64-9 ]
(S)-2,4-diamino-6-((1-(5-chloro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile 2,2,2-trifluoroacetic acid Salt [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

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[ 3029-64-9 ]
(S)-2,4-diamino-6-((1-(5-chloro-3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

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[ 1615252-78-2 ]

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[ 1615251-79-0 ]

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[ 1615251-83-6 ]

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[ 1615253-34-3 ]

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[ 3029-64-9 ]
[ 1615252-18-0 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

36
[ 3029-64-9 ]
[ 1615252-90-8 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

37
[ 3029-64-9 ]
(S)-2,4-diamino-6-((1-(5-chloro-3-(3-(difluoromethyl)phenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl)amino)-pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

38
[ 3029-64-9 ]
[ 1615252-58-8 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

39
[ 3029-64-9 ]
[ 1615252-85-1 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3532 - 3548

40
[ 76697-50-2 ]
[ 3029-64-9 ]
C₁₄H₁₂Cl₂N₄O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1090 - 1096

41
[ 76697-50-2 ]
[ 3029-64-9 ]
[ 1190399-79-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1090 - 1096

42
[ 3029-64-9 ]
((S)-2,4-diamino-6-((1-(5-chloro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

43
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-3-(5-fluoropyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

44
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-3-(5-chloropyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

45
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-3-(5-methoxypyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

46
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-3-(5-cyclopropylpyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

47
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-4-oxo-3-(5-(trifluoromethyl)-pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)ethylamino)-pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

48
[ 3029-64-9 ]
(S)-2,4-diamino-6-((1-(5-chloro-3-(5-cyanopyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

49
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)propylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

50
[ 3029-64-9 ]
(S)-2-chloro-6-(2-((2,6-diamino-5-cyanopyrimidin-4-yl)-amino)propanamido)-N-(pyridin-3-yl)benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

51
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-3-(2-methylpyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

52
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-3-(4-methylpyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

53
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-3-(5-fluoro-4-methylpyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethylamino)-pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

54
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(8-chloro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

55
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5,8-dichloro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

56
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5,8-difluoro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

57
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-8-fluoro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

58
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-8-fluoro-3-(5-fluoropyridin-3-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

59
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(5-chloro-8-fluoro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)propylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

60
[ 3029-64-9 ]
(S)-2,4-diamino-6-(((5-chloro-8-fluoro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl) (cyclopropyl)methyl)amino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 9228 - 9242

61
[ 3029-64-9 ]
(S)-2,4-diamino-6-((1-(5-chloro-4-oxo-3-(1H-pyrazol-3-yl)-3,4-dihydroquinazolin-2-yl)ethyl)amino)-pyrimidine-5-carbonitrile 2,2,2-trifluoroacetic acid salt [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1555 - 1567

62
[ 3029-64-9 ]
(S)-2,4-diamino-6-(((8-chloro-6-fluoro-4-oxo-3-(1H-pyrazol-3-yl)-3,4-dihydroquinazolin-2-yl)(cyclopropyl)methyl)amino)-pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1555 - 1567

63
[ 3029-64-9 ]
(S)-2,4-diamino-6-{1-[7-fluoro-2-(3-fluorophenyl)quinolin-3-yl]ethylamino}pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2017/155741,2017,A1

64
[ 3029-64-9 ]
2,4,6-triazidopyrimidine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium azide; In water; acetone; for 6h;Heating;	The mixture of trichloride 8 (4.17 g, 20 mmol) and sodium azide (5.2 g, 80 mmol) in 150 mL of aq. Acetone (5percent of water) was boiled for 6 h, then the solvent was removed under vacuum, and a solid residue was washed with water (200 mL), dried on air and recrystallized. Triazide 9 was obtained as a colorless solid (3.74 g, 82percent). mp 118-120 °C (EtOH). IR (microcrystals, max/cm?1): 2235m, 2213m, 2160vs, 2133s, 2096m, 1562s, 1530vs, 1421s, 1371vs, 1280w, 1239s, 1209vs, 1156m, 1136m, 1083w, 1030w, 1006m, 969w, 811m, 782vs, 742s, 696w. UV-vis,max /nm (log ): 249 (4.03), 275 (3.55), 295 (3.46), 304 (3.42). 13C-NMR: 80.9, 110.4, 162.7, 166.9. 15N-NMR: ?99.8, ?130.2, ?132.4, ?142.3, ?144.2, ?148.6, ?257.0, ?259.7. EIMS, 70 eV, m/z (rel.int.): 229 (4, M++1), 228 (30, M+), 92 (7, C3N4+), 90 (8, C4N3+), 78 (100, C3N3+), 68 (5, CN4+), 66 (31, C2N3+), 64 (70, C3N2+), 54 (11, CN3+), 52 (35, C2N2+), 50 (12, C3N+), 42 (12, N3+), 40 (18, CN2+), 38 (46, C2N+), 26 (9, CN+). Anal. Calcd. for C5N12 (228.13): C, 26.32; N, 73.68. Found: C, 26.55; N, 73.45percent.

Reference： [1]Arkivoc,2018,vol. 2018,p. 39 - 50

65
[ 3029-64-9 ]
2,4,6-triazidopyrimidine-5-carbonitrile [ No CAS ]
4,6-diazido-2-chloropyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Arkivoc,2018,vol. 2018,p. 39 - 50

66
[ 135-67-1 ]
[ 3029-64-9 ]
C₄₁H₂₄N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.3%		6.37 g (35 mmol) of phenoxazine was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent, and the mixture was stirred on a magnetic stirrer for 10 min under ice bath. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.Dissolve 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> in 40 mlThe N,N-dimethylformamide solution was added dropwise to the reaction system, and after the addition was completed, the reaction was carried out at room temperature for 24 hours. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 3.91 g of a white solid powder was obtained in a yield of 60.3percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0089; 0090

67
[ 3029-64-9 ]
10,10-dimethyl-5,10-dihydrodibenzo[b,e][1,4]azasiline [ No CAS ]
C₄₇H₄₂N₆Si₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.9%		7.84 g (35 mmol) of 10,10-dimethyl-diphenyl phenyl siloxane was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent in an ice bath condition. Next, stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 3.94 g of a white solid powder was obtained in a yield of 50.9percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0091; 0092

68
[ 49662-17-1 ]
[ 3029-64-9 ]
C₅₉H₃₉N₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.8%		9.00 g (35 mmol) of 10-phenylphenol azine was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent under ice bath conditions.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 4.87 g of a white solid powder was obtained in a yield of 55.8percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0093; 0094; 0095

69
[ 56525-79-2 ]
[ 3029-64-9 ]
C₇₇H₄₈N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.3%		11.17 g (35 mmol) of 3,6-diphenyloxazole was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent under ice bath conditions.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.2.07 g (10 mmol) of 2,4,6-trichloro-5-cyanopyrimidine was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 5.31 g of a white solid powder was obtained in a yield of50.3percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0102; 0103; 0104

70
[ 92-84-2 ]
[ 3029-64-9 ]
C₄₁H₂₄N₆S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.7%		6.93 g (35 mmol) of thiazideAdd to a 250 ml three-necked flask and add 100 ml of N,N-dimethylformamide as the reaction solvent in an ice bath.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added in portions to the reaction flaskIn the middle, continue stirring for 1 h.Dissolve 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> in 40 ml of N,N-dimethylformylThe amine solution was added dropwise to the reaction system, and after the addition was completed, the reaction was carried out at room temperature for 24 hours. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 4.64 g of a white solid powder was obtained in a yield of 66.7percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0105; 0106

71
3,6-diisopropylcarbazole [ No CAS ]
[ 3029-64-9 ]
C₄₁H₄₀ClN₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In toluene; for 1h;Reflux; Inert atmosphere;	Under nitrogen protection, 6.28 g (25 mmol) of isopropyl carbazole,2.83 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong>, 1.92 g (20 mmol) of NaOBu-t, 1.92 g (0.2 mmol) (t-Bu)3HBF4, 0.09 g (0.1 mmol) Pd2 ( Dba) 3 was added to a 250 ml three-necked flask, 100 ml of toluene was added as a reaction solvent, the temperature was raised to reflux temperature, and the mixture was stirred overnight on a magnetic stirrer. After completion of the reaction, the reaction solution was dried to dryness, and the obtained crude product was purified from petroleum ether and methylene chloride (PE: DCM = 5:1) as a mobile phase. Intermediate 1 was obtained as a white solid powder weighing 4.70 g, yield 73.7percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0082; 0083; 0084

72
3,6-diisopropylcarbazole [ No CAS ]
[ 3029-64-9 ]
C₅₆H₅₄N₆ [ No CAS ]

Reference： [1]Patent: CN109553606,2019,A

73
3,6-diisopropylcarbazole [ No CAS ]
[ 3029-64-9 ]
C₅₉H₆₀N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.2%		8.79 g (35 mmol) of isopropyl carbazole was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent, and the mixture was stirred on a magnetic stirrer for 10 min under ice-cooling. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. A white solid powder of 5.56 g was obtained in a yield of 65.2percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0075; 0076; 0077

74
[ 3029-64-9 ]
[ 606129-90-2 ]
C₁₁₃H₆₆N₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.2%		8.79 g (35 mmol) of isopropyl carbazole was added to a 250 ml three-necked flask, and 100 ml of N,N-dimethylformamide was added as a reaction solvent in an ice bath.Stir on a magnetic stirrer for 10 min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h.4.97 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. Obtained 7.98 g of a white solid powder in a yield of50.2percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0107; 0108; 0109

75
[ 6267-02-3 ]
[ 3029-64-9 ]
C₅₀H₄₂N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.1%		7.32 g (35 mmol) of 9,9-dimethyl acridine was added to a 250 ml three-necked flask, 100 ml of N,N-dimethylformamide was added as a reaction solvent, and the mixture was stirred on a magnetic stirrer in an ice bath. 10min. 0.72 g (30 mmol) of NaH was added portionwise to the reaction flask and stirring was continued for 1 h. 2.07 g (10 mmol) of <strong>[3029-64-9]2,4,6-trichloro-5-cyanopyrimidine</strong> was dissolved in 40 ml of N,N-dimethylformamide solution, and added dropwise to the reaction system. After the addition, at room temperature The reaction was carried out for 24 h. After the reaction was completed, the reaction solution was poured into 200 ml of 10percent diluted hydrochloric acid, and the mixture was filtered under reduced pressure, washed with water and dried, and the crude product was obtained from petroleum ether and dichloromethane (PE: DCM=10: 1) Pass the column for the mobile phase. 4.29 g of a white solid powder was obtained in a yield of 59.1percent.

Reference： [1]Patent: CN109553606,2019,A .Location in patent: Paragraph 0087; 0088

76
[ 3029-64-9 ]
6-(1H-pyrazol-4-yl)-4,4-dimorpholine-5-cyanopyrimidine [ No CAS ]

Reference： [1]Patent: CN109651341,2019,A

77
[ 110-91-8 ]
[ 3029-64-9 ]
C₁₃H₁₆ClN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; at -20 - 20℃; for 3h;	Solution of compound 1a (1mmol) was dissolved in 5ml of anhydrous tetrahydrofuran was added dropwise at -20C morpholine (4.5 mmol), dropwise warmed to room temperature for 3 hours, add 5ml of water to precipitate a white solid which was filtered, the filter cake was washed with ethanol weight crystallization or petroleum ether / ethyl acetate (5: 1) column chromatography to give compound 2a.

Reference： [1]Patent: CN109651341,2019,A .Location in patent: Paragraph 0037; 0039-0040; 0060; 0061

78
[ 50270-27-4 ]
[ 3029-64-9 ]

Yield	Reaction Conditions	Operation in experiment
92%		Step 2. 2,4,6-trichloropyrimidin-5-formonitrile 2,4,6-trichloropyrimidin-5-carboxaldehyde (10 g, 47.4 mmol), hydroxylamine hydrochloride (3.3 g, 47.5 mmol), glacial acetic acid (100 mL), and H2O (5 mL) were added to a 150-mL round-bottom flask, and heated to 60 C. to react for 1 hour. After the completion of the reaction, the reaction solution was poured into crushed ice, and was extracted with CH2Cl2. The resultant organic phases were combined, washed with a saturated NaCl solution, dried with anhydrous Na2SO4, and then filtered and concentrated. The obtained substance was dissolved in SOCl2 (60 mL), reacted at room temperature for 10 minutes, and then heated for a reflux reaction for 2 hours. After the completion of the reaction, the resultant mixture was subjected to reduced pressure distillation to remove SOCl2 to give a residue, which was then dissolved in EtOAc and washed with H2O. The resultant organic phase was dried with anhydrous Na2SO4, filtered, and concentrated to obtain an oily substance of 9 g. The yield was 92%.

Reference： [1]Patent: US2019/255057,2019,A1 .Location in patent: Paragraph 0086; 0088

79
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(3-chloro-5-phenylpyrazolo[1,5-a]pyrimidin-6-yl)ethylamino)pyrimidin-5-formonitrile [ No CAS ]

Reference： [1]Patent: US2019/255057,2019,A1

80
[ 3029-64-9 ]
(S)-2,4-diamino-6-(1-(3-chloro-5-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-6-yl)ethylamino)pyrimidin-5-formonitrile [ No CAS ]

Reference： [1]Patent: US2019/255057,2019,A1

81
(R)-cyclopropyl (2-methylpiperazin-1-yl)methanone [ No CAS ]
[ 3029-64-9 ]
(R)-4,6-dichloro-2-(4-(cyclopropanecarbonyl)-3-methylpiperazin-1-yl)pyrimidine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at -40℃; for 2h;Inert atmosphere;	To a solution of 2, 4, 6-trichloropyrimidine-5-carbonitrile (25-a) (2.00 g, 9.60 mmol) in DMF (20 ml) at -40 under an atmosphere of nitrogen, was added trimethylamine (Et3N) (2.67 ml, 19.2 mmol) and (R) -cyclopropyl (2-methylpiperazin-1-yl) methanone (12-IA) (1.61 g, 9.60 mmol) . The resulting mixture was stirred for 2 h. After 2 h, the reaction was quenched via the addition of water (50 mL) and allowed to warm to ambient temperature. The mixture was extracted with EtOAc (3 x 100 mL) . The combined organic layers were washed with brine (100 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified via silica gel chromatography (50 g, 100-200 mesh) , eluting with 0-30%EtOAc in hexane to afford (R) -4, 6-dichloro-2- (4- (cyclopropanecarbonyl) -3-methylpiperazin-1-yl) pyrimidine-5-carbonitrile (25-c) . MS (ESI) Calc?d for (C14H16Cl2N5O) [M+H]+, 340; found, 340.

Reference： [1]Patent: WO2019/119206,2019,A1 .Location in patent: Page/Page column 86-87

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Nitriles

[ 5305-45-3 ]

4,6-Dichloropyrimidine-5-carbonitrile

Similarity: 0.91

[ 3177-24-0 ]

2,4-Dichloropyrimidine-5-carbonitrile

Similarity: 0.87

[ 1277179-33-5 ]

2-Amino-4,6-dichloropyrimidine-5-carbonitrile

Similarity: 0.82

[ 33097-13-1 ]

4,6-Dichloro-2-(methylthio)pyrimidine-5-carbonitrile

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[ 1753-50-0 ]

2-Chloropyrimidine-5-carbonitrile

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Related Parent Nucleus of
[ 3029-64-9 ]

Pyrimidines

[ 5305-45-3 ]

4,6-Dichloropyrimidine-5-carbonitrile

Similarity: 0.91

[ 1780-36-5 ]

2,4,6-Trichloro-5-methylpyrimidine

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[ 3177-24-0 ]

2,4-Dichloropyrimidine-5-carbonitrile

Similarity: 0.87

[ 1277179-33-5 ]

2-Amino-4,6-dichloropyrimidine-5-carbonitrile

Similarity: 0.82

[ 50270-27-4 ]

2,4,6-Trichloropyrimidine-5-carbaldehyde

Similarity: 0.81

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
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
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
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.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
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:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
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.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
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

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. 3029-64-9 ] {[proInfo.proName]}

Quality Control of [ 3029-64-9 ]

Related Doc. of [ 3029-64-9 ]

Product Details of [ 3029-64-9 ]

Calculated chemistry of [ 3029-64-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3029-64-9 ]

Application In Synthesis of [ 3029-64-9 ]

[ 3029-64-9 ] Synthesis Path-Upstream 1~1

[ 3029-64-9 ] Synthesis Path-Downstream 1~81

Related Functional Groups of [ 3029-64-9 ]

Chlorides

Nitriles

Related Parent Nucleus of [ 3029-64-9 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3029-64-9 ]

Related Parent Nucleus of
[ 3029-64-9 ]