[ CAS No. 3709-98-6 ] {[proInfo.proName]}

Name: 3709-98-6|2-Ethyl-4,6-dihydroxypyrimidine|95%
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SKU: A107138
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Quality Control of [ 3709-98-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3709-98-6 ]

Product Details of [ 3709-98-6 ]

CAS No. :	3709-98-6	MDL No. :	MFCD09907955
Formula :	C₆H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CBXPKEZRCKCOID-UHFFFAOYSA-N
M.W :	140.14	Pubchem ID :	520836
Synonyms :

Calculated chemistry of [ 3709-98-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	35.85
TPSA :	66.24 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.59
Log Po/w (XLOGP3) :	0.99
Log Po/w (WLOGP) :	0.45
Log Po/w (MLOGP) :	-0.52
Log Po/w (SILICOS-IT) :	0.68
Consensus Log Po/w :	0.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.71
Solubility :	2.73 mg/ml ; 0.0195 mol/l
Class :	Very soluble
Log S (Ali) :	-1.97
Solubility :	1.5 mg/ml ; 0.0107 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.27
Solubility :	7.58 mg/ml ; 0.0541 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 3709-98-6 ]

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

Application In Synthesis of [ 3709-98-6 ]

* 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 [ 3709-98-6 ]
Downstream synthetic route of [ 3709-98-6 ]

[ 3709-98-6 ] Synthesis Path-Upstream 1~4

1
[ 3599-89-1 ]
[ 105-53-3 ]
[ 3709-98-6 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: With sodium methylate In methanol at 10 - 35℃; for 0.166667 h; Stage #2: at 10 - 35℃; for 16 h;	Reference Example 29 Production of 2-ethylpyrimidine-4,6-diol To a solution of the compound of Reference Example 28 (11 g, 99 mmol) in methanol (20 mL) was added 28percent methanol solution (57 g, 296 mmol) of sodium methoxide, and the mixture was stirred at room temperature for 10 min. Diethyl malonate (15 mL, 99 mmol) was added dropwise thereto, and the mixture was further stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water, and the solution was acidified with concentrated hydrochloric acid. The precipitated solid was collected by filtration, washed with water and diethyl ether and dried to give the title compound (9.3 g, 67percent) as white crystals. ¹H NMR (300 MHz, DMSO-d₆) δ:1.16 (3 H, t, J = 7.6 Hz), 2.36 - 2.60 (2 H, m), 5.03 (1 H, s), 11. 62 (2 H, br s).
67%	Stage #1: With sodium methylate In methanol at 20℃; for 0.166667 h; Stage #2: at 20℃; for 16 h;	5.2 2-Ethylpyrimidine-4,6-diol (9) To a solution of 8 (11 g, 99 mmol) in MeOH (20 mL) was added 28percent solution of NaOMe in MeOH (57 g, 296 mmol), and the mixture was stirred at room temperature for 10 min. Diethyl malonate (15 mL, 99 mmol) was added dropwise, and the mixture was further stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo, the residue was dissolved in water and acidified with concd HCl. The precipitated solid was collected by filtration, washed with water and Et₂O to give the title compound (9.3 g, 67percent) as a white solid. ¹H NMR (DMSO-d₆) δ 1.16 (3H, t, J = 7.6 Hz), 2.36-2.60 (2H, m), 5.03 (1H, s), 11.62 (2H, br s).
38%	Stage #1: With sodium In methanol for 0.25 h; Cooling with ice Stage #2: at 20℃; for 4 h;	Sodium (1.27 g, 55.3 mmcl) was added to anhydrous methanol (50 mL) under ice bath. Once sodium was completely dissolved propionimidamide hydrochloride (2.00 g, 18.4 mmol)was added and the reaction mixture was stirred for 15 mm. Then diethyl malonate (3.80 g,23.9 mmcl) was added dropwise. The reaction mixture was warmed to ri and stirred for 4 hrs. The mixture was concentrated under vacuum. The resulting residue was dissolved in water (120 mL) and the solution was acidified with conc. HCI to pH = 5. The mixture was filtered and the solid was collected. The solid was successively washed with H20 (15 mL),isopropanol (10 ml) and PE (10 ml), and dried under vacuum to afford the title compound(0.96 g, yield: 38percent) as a white solid.1H NMR (300 MHz, DMSO-d6): ö 11.59(brs, 2H), 5.01 (s, IH), 2.46(q, J 7.8 Hz, 2H), 0.97(t, J = 7.8 Hz, 3H).LC-MS: 5-95percent CH3CN in 3 mm, Rt = 0.25 mm; MS Calcd.:140, MS Found: 141 [M+H].

Reference： [1] Patent: EP2471793, 2012, A1, . Location in patent: Page/Page column 48
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4777 - 4791
[3] Patent: WO2017/12576, 2017, A1, . Location in patent: Page/Page column 77

2
[ 3599-89-1 ]
[ 108-59-8 ]
[ 3709-98-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium methylate In methanol; water	Part B1. Preparation of 4,6-Dihydroxy-2-ethylpyrimidine according to Step (1) To a cooled, stirred solution of 25percent sodium methoxide (1200 ml, 5.55 mole) was added a slurry of 200 g (1.85 mole) of propionamidine hydrochloride in 300 ml of methanol. Next, 244 g (1.85 mole) of dimethyl malonate was added and the mixture was permitted to warm to about 20° C., after which it was stirred for 16 hours. The mixture was evaporated in vacuo and water (about 2 l) was added. This mixture was neutralized with concentrated hydrochloric acid to provide a white precipitate which was separated by filtration to provide 230 g (96percent) of 4,6-dihydroxy-2-ethylpyrimidine, m.p. 312°-215° C. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Reference： [1] Patent: US4536579, 1985, A,
[2] Patent: WO2013/28590, 2013, A1, . Location in patent: Page/Page column 63; 64

3
[ 108-59-8 ]
[ 3709-98-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium methylate In methanol; water	Part B1. Preparation of 4,6-Dihydroxy-2-ethylpyrimidine according to Step (1) To a cooled, stirred solution of 25percent sodium methoxide (1200 ml, 5.55 mole) was added a slurry of 200 g (1.85 mole) of propionamide hydrochloride in 300 ml of methanol. Next, 244 g (1.85 mole) of dimethyl malonate was added and the mixture was permitted to warm to about 20° C., after which it was stirred for 16 hours. The mixture was evaporated in vacuo and water (about 2 l) was added. This mixture was neutralized with concentrated hydrochloric acid to provide a white precipitate which was separated by filtration to provide 230 g (96percent) of 4,6-dihydroxy-2-ethylpyrimidine, m.p. 312°-315° C. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Reference： [1] Patent: US4477450, 1984, A,

4
[ 108-59-8 ]
[ 3709-98-6 ]

Reference： [1] Patent: US4477450, 1984, A,
[2] Patent: US4536579, 1985, A,

[ 3709-98-6 ] Synthesis Path-Downstream 1~32

2
[ 108-59-8 ]
[ 3709-98-6 ]

Yield	Reaction Conditions	Operation in experiment
16.5 g (89.5%)		Part B2. Alternative Preparation of 4,6-Dihydroxy-2-ethylpyrimidine Using the procedure of Example 1, Part B1, 18.5 g (0.14 mole) of propionamidine acetate and 90 ml of 25% sodium methoxide were reacted with dimethyl malonate (0.14 mole) to provide 16.5 g (89.5%) of 4,6-dihydroxy-2-ethylpyrimidine according to Step (1).
16.5 g (89.5%)		Alternative Preparation of 4,6-Dihydroxy-2-ethylpyrimidine Using the procedure of Example 1, Part B1, 18.5 g (0.14 mole) of propionamidine acetate and 90 ml of 25% sodium methoxide were reacted with dimethyl malonate (0.14 mole) to provide 16.5 g (89.5%) of 4,6-dihydroxy-2ethylpyrimidine according to Step (1).

Reference： [1]Patent: US4477450,1984,A
[2]Patent: US4536579,1985,A

3
[ 3599-89-1 ]
[ 108-59-8 ]
[ 3709-98-6 ]

Yield	Reaction Conditions	Operation in experiment
230 g (96%)	With sodium methylate; In methanol; water;	Part B1. Preparation of 4,6-Dihydroxy-2-ethylpyrimidine according to Step (1) To a cooled, stirred solution of 25% sodium methoxide (1200 ml, 5.55 mole) was added a slurry of 200 g (1.85 mole) of propionamidine hydrochloride in 300 ml of methanol. Next, 244 g (1.85 mole) of dimethyl malonate was added and the mixture was permitted to warm to about 20 C., after which it was stirred for 16 hours. The mixture was evaporated in vacuo and water (about 2 l) was added. This mixture was neutralized with concentrated hydrochloric acid to provide a white precipitate which was separated by filtration to provide 230 g (96%) of 4,6-dihydroxy-2-ethylpyrimidine, m.p. 312-215 C. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.
		To a stirred solution of propionimidamide hydrochloride (1.00 g, 9.21 mmol) in ethanol (35 mL) was added sodium ethoxide solution 21% in ethanol (17.25 mL). The resulting solution was stirred 20 minutes at room temperature. To this was added dimethyl malonate (0.97 g, 7.37 mmol) and the resulting solution was heated to 80C for 5 hours. The solution was allowed to cool and concentrated to dryness. To this solid was added a minimum amount of water and neutralized to pH of 5 using 6N HCl solution. The solution was allowed to sit overnight during which time white solid 3-1 precipitated out. The solid 3-1 was dissolved in phosphorus oxychloride (5 mL) and heated to reflux for 90 minutes. The solution was concentrated, quenched with ice, and partitioned between ethyl acetate and a saturated sodium bicarbonate solution. The organic phase was concentrated to give 3-2 as an oil (0.60 g, 37%). LRMS (M+H)+: observed = 177.1, calculated = 177.0.

Reference： [1]Patent: US4536579,1985,A
[2]Patent: WO2013/28590,2013,A1 .Location in patent: Page/Page column 63; 64

4
[ 108-59-8 ]
propionamide hydrochloride [ No CAS ]
[ 3709-98-6 ]

Yield	Reaction Conditions	Operation in experiment
230 g (96%)	With sodium methylate; In methanol; water;	Part B1. Preparation of 4,6-Dihydroxy-2-ethylpyrimidine according to Step (1) To a cooled, stirred solution of 25% sodium methoxide (1200 ml, 5.55 mole) was added a slurry of 200 g (1.85 mole) of propionamide hydrochloride in 300 ml of methanol. Next, 244 g (1.85 mole) of dimethyl malonate was added and the mixture was permitted to warm to about 20 C., after which it was stirred for 16 hours. The mixture was evaporated in vacuo and water (about 2 l) was added. This mixture was neutralized with concentrated hydrochloric acid to provide a white precipitate which was separated by filtration to provide 230 g (96%) of 4,6-dihydroxy-2-ethylpyrimidine, m.p. 312-315 C. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Reference： [1]Patent: US4477450,1984,A

5
[ 3709-98-6 ]
[ 1195-34-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With trichlorophosphate; at 100℃; for 2h;	To a flask (50 mL) containing <strong>[3709-98-6]2-ethylpyrimidine-4,6-diol</strong> (963 mg, 6.87 mmol) was added POCI3 (10 mL). Then the mixture was heated to 100 C for 2 hrs. The mixture was cooled tort and poured into water (100 mL) and basified with saturated NaHCO3 to pH = 6-7. Then the mixture was extracted with ethyl acetate (40 mL x 2). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column (PE: EtOAc = 20: 1) give the title compound (920 mg, yield 76%) as a colorless oil.1H NMR (300 MHz, CDCI3): 67.25 (s, 1H), 2.95 (q, J 7.8 Hz, 2H), 1.35 (t, J=7.8 Hz, 3H).
41 g (70%)	With trichlorophosphate; In ice-water;	Part C. Preparation of 4,6-Dichloro-2-ethylpyrimidine A mixture of 150 g (1.15 mole) of <strong>[3709-98-6]4,6-dihydroxy-2-ethylpyrimidine</strong> and 1073 g (7.0 mole, 640 ml) of phosphorus oxychloride was heated at reflux for 6 hours, cooled and evaporated in vacuo to provide a brown oil as the residue. The residue was poured into 1500 ml of an ice-water mixture. The mixture was extracted thrice with 400 ml portions of diethyl ether. The combined ether extracts were washed sequentially with water (200 ml), 5% sodium hydroxide solution (twice with 200 ml portions), and saturated sodium chloride solution (200 ml), and were then dried over magnesium sulfate. Evaporation of the ether provided an oil which was distilled to provide 41 g (70%) of 4,6-dichloro-2-ethylpyrimidine, b.p. 55-60 C/1.5 to 4 mm Hg. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.
41 g (70%)	With trichlorophosphate; In ice-water;	Part C. Preparation of 4,6-Dichloro-2-ethylpyrimidine A mixture of 150 g (1.15 mole) of 4,6-dihydroxyl-2-ethylpyrimidine and 1073 g (7.0 mole, 640 ml) of phosphorus oxychloride was heated at reflux for 6 hours, cooled and evaporated in vacuo to provide a brown oil as the residue. The residue was poured into 1500 ml of an ice-water mixture. The mixture was extracted thrice with 400 ml portions of diethyl ether. The combined ether extracts were washed sequentially with water (200 ml), 5% sodium hydroxide solution (twice with 200 ml portions), and saturated sodium chloride solution (200 ml), and were then dried over magnesium sulfate. Evaporation of the ether provided an oil which was distilled to provide 41 g (70%) of 4,6-dichloro-2-ethylpyrimidine, b.p. 55-60 C/1.5 to 4 mm Hg. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

With trichlorophosphate; for 1.5h;Reflux;

To a stirred solution of propionimidamide hydrochloride (1.00 g, 9.21 mmol) in ethanol (35 mL) was added sodium ethoxide solution 21% in ethanol (17.25 mL). The resulting solution was stirred 20 minutes at room temperature. To this was added dimethyl malonate (0.97 g, 7.37 mmol) and the resulting solution was heated to 80C for 5 hours. The solution was allowed to cool and concentrated to dryness. To this solid was added a minimum amount of water and neutralized to pH of 5 using 6N HCl solution. The solution was allowed to sit overnight during which time white solid 3-1 precipitated out. The solid 3-1 was dissolved in phosphorus oxychloride (5 mL) and heated to reflux for 90 minutes. The solution was concentrated, quenched with ice, and partitioned between ethyl acetate and a saturated sodium bicarbonate solution. The organic phase was concentrated to give 3-2 as an oil (0.60 g, 37%). LRMS (M+H)+: observed = 177.1, calculated = 177.0.

Reference： [1]Patent: WO2017/12576,2017,A1 .Location in patent: Page/Page column 77; 78
[2]Patent: US4477450,1984,A
[3]Patent: US4536579,1985,A
[4]Patent: WO2013/28590,2013,A1 .Location in patent: Page/Page column 63; 64

6
[ 3599-89-1 ]
[ 105-53-3 ]
[ 3709-98-6 ]

Yield	Reaction Conditions	Operation in experiment
67%		Reference Example 29 Production of 2-ethylpyrimidine-4,6-diol To a solution of the compound of Reference Example 28 (11 g, 99 mmol) in methanol (20 mL) was added 28% methanol solution (57 g, 296 mmol) of sodium methoxide, and the mixture was stirred at room temperature for 10 min. Diethyl malonate (15 mL, 99 mmol) was added dropwise thereto, and the mixture was further stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water, and the solution was acidified with concentrated hydrochloric acid. The precipitated solid was collected by filtration, washed with water and diethyl ether and dried to give the title compound (9.3 g, 67%) as white crystals. 1H NMR (300 MHz, DMSO-d6) delta:1.16 (3 H, t, J = 7.6 Hz), 2.36 - 2.60 (2 H, m), 5.03 (1 H, s), 11. 62 (2 H, br s).
67%		5.2 2-Ethylpyrimidine-4,6-diol (9) To a solution of 8 (11 g, 99 mmol) in MeOH (20 mL) was added 28% solution of NaOMe in MeOH (57 g, 296 mmol), and the mixture was stirred at room temperature for 10 min. Diethyl malonate (15 mL, 99 mmol) was added dropwise, and the mixture was further stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo, the residue was dissolved in water and acidified with concd HCl. The precipitated solid was collected by filtration, washed with water and Et2O to give the title compound (9.3 g, 67%) as a white solid. 1H NMR (DMSO-d6) delta 1.16 (3H, t, J = 7.6 Hz), 2.36-2.60 (2H, m), 5.03 (1H, s), 11.62 (2H, br s).
38%		Sodium (1.27 g, 55.3 mmcl) was added to anhydrous methanol (50 mL) under ice bath. Once sodium was completely dissolved propionimidamide hydrochloride (2.00 g, 18.4 mmol)was added and the reaction mixture was stirred for 15 mm. Then diethyl malonate (3.80 g,23.9 mmcl) was added dropwise. The reaction mixture was warmed to ri and stirred for 4 hrs. The mixture was concentrated under vacuum. The resulting residue was dissolved in water (120 mL) and the solution was acidified with conc. HCI to pH = 5. The mixture was filtered and the solid was collected. The solid was successively washed with H20 (15 mL),isopropanol (10 ml) and PE (10 ml), and dried under vacuum to afford the title compound(0.96 g, yield: 38%) as a white solid.1H NMR (300 MHz, DMSO-d6): oe 11.59(brs, 2H), 5.01 (s, IH), 2.46(q, J 7.8 Hz, 2H), 0.97(t, J = 7.8 Hz, 3H).LC-MS: 5-95% CH3CN in 3 mm, Rt = 0.25 mm; MS Calcd.:140, MS Found: 141 [M+H].

Reference： [1]Patent: EP2471793,2012,A1 .Location in patent: Page/Page column 48
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791
[3]Patent: WO2017/12576,2017,A1 .Location in patent: Page/Page column 77

7
[ 3709-98-6 ]
[ 1269118-42-4 ]

Reference： [1]Patent: EP2471793,2012,A1
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

8
[ 3709-98-6 ]
[ 1269118-46-8 ]

Reference： [1]Patent: EP2471793,2012,A1
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

9
[ 68-12-2 ]
[ 3709-98-6 ]
[ 1269118-40-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With trichlorophosphate; at 10℃; for 17h;Reflux;	Reference Example 30 Production of 4,6-dichloro-2-ethylpyrimidine-5-carbaldehyde Under ice-cooling, DMF (5.5 mL) was added dropwise to phosphorus oxychloride (60 mL, 641 mmol), and the mixture was stirred at 0C for 1 hr. The compound of Reference Example 29 (10 g, 71 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was heated under reflux for 16 hr, and concentrated under reduced pressure. The residue was added to ice water by small portions, and the mixture was extracted 3 times with a mixed solvent of diethyl ether-ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was suspended in ethyl acetate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluate, ethyl acetate:hexane=1:99?10:90) to give the title compound (10.6 g, 73%) as a pale-yellow powder. 1H NMR (300 MHz, CDCl3) delta:1.32 - 1.48 (3 H, m), 2.91 - 3.13 (2 H, m), 10.25 - 10.63 (1 H, m).
73%		5.3 Ethyl 4,6-dichloro-2-ethylpyrimidine-5-carboxylate (6a) DMF (5.5 mL) was added dropwise to POCl3 (60 mL, 641 mmol) at 0 C, the mixture was stirred at 0 C for 1 h. 9 (10 g, 71 mmol) was added, the mixture was stirred at room temperature for 1 h and heated under reflux for 16 h. The mixture was concentrated in vacuo, the residue was added to ice water by small portions. The mixture was extracted three times with a mixed solvent of Et2O/AcOEt. The extracts were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was suspended in AcOEt, and the insoluble material was filtered off. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/AcOEt = 99/1 to 9/1) to give 4,6-dichloro-2-ethylpyrimidine-5-carbaldehyde (10.6 g, 73%) as a pale yellow powder. To a mixture of obtained aldehyde (11 g,52 mmol), amidosulfuric acid (7.0 g, 72 mmol), tert-butanol(100 mL) and water (40 mL) was added dropwise a solution ofsodium chlorite (6.6 g, 72 mmol) in water (20 mL). After stirringat room temperature for 30 min, the reaction mixture was dilutedwith water, and extracted twice with AcOEt. The extracts werecombined, washed with water and brine, dried over MgSO4 andconcentrated in vacuo. The residue was dissolved in THF (60 mL),oxalyl chloride (9.7 mL, 111 mmol) was added dropwise at 0 C,then DMF (1 drop) was added. After stirring at room temperaturefor 3 h, the reaction mixture was concentrated in vacuo. EtOH(60 mL) and Et3N (16 mL, 111 mmol) were added under ice-cooling,and the mixture was stirred at room temperature for 3 h.The reaction mixture was diluted with saturated NaHCO3 aq andwater, and extracted twice with AcOEt. The extracts were combined,washed with brine, dried over MgSO4 and concentrated invacuo. The residue was purified by silica gel column chromatography(hexane/AcOEt = 97/3 to 17/3) to give the title compound(6.7 g, 53%) as pale yellow oil. 1H NMR (CDCl3) d 1.31-1.48 (6H,m), 2.97 (2H, q, J = 7.6 Hz), 4.48 (2H, q, J = 7.2 Hz).

Reference： [1]Patent: EP2471793,2012,A1 .Location in patent: Page/Page column 49
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

10
[ 3709-98-6 ]
[ 1269117-06-7 ]

Reference： [1]Patent: EP2471793,2012,A1

11
[ 3709-98-6 ]
[ 1269118-48-0 ]

Reference： [1]Patent: EP2471793,2012,A1
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

12
[ 3709-98-6 ]
[ 1269118-49-1 ]

Reference： [1]Patent: EP2471793,2012,A1
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

13
[ 3709-98-6 ]
[ 1269118-51-5 ]

Reference： [1]Patent: EP2471793,2012,A1
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

14
[ 3709-98-6 ]
[ 1269118-87-7 ]

Reference： [1]Patent: EP2471793,2012,A1

15
[ 3709-98-6 ]
[ 1269118-89-9 ]

Reference： [1]Patent: EP2471793,2012,A1

16
[ 3709-98-6 ]
[ 1269118-90-2 ]

Reference： [1]Patent: EP2471793,2012,A1

17
[ 3709-98-6 ]
[ 1269118-91-3 ]

Reference： [1]Patent: EP2471793,2012,A1

18
[ 3709-98-6 ]
[ 1269118-94-6 ]

Reference： [1]Patent: EP2471793,2012,A1

19
[ 3709-98-6 ]
[ 1269118-44-6 ]

Reference： [1]Patent: EP2471793,2012,A1
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

20
[ 3709-98-6 ]
C₇H₅Cl₃N₂O*(x)ClH [ No CAS ]

Reference： [1]Patent: EP2471793,2012,A1

21
[ 3709-98-6 ]
[ 1269118-55-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

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[ 3709-98-6 ]
[ 1269116-89-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

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[ 3709-98-6 ]
[ 1269118-54-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

24
[ 3709-98-6 ]
ethyl 2-ethyl-7-methyl-4-oxo-3-(2-oxo-2-phenylethyl)-5-(2,2,2-trifluoroethoxy)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-6-carboxylate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4777 - 4791

25
[ 3709-98-6 ]
4-(2-ethyl-6-(5-methyl-6-(4-methylpiperazin-1-yl)-1H-indazol-1-yl)pyrimidin-4-yl)morpholine [ No CAS ]