[ CAS No. 5194-32-1 ] {[proInfo.proName]}

Name: 5194-32-1|2-Methylpyrimidine-5-carboxylic acid|97%
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Quality Control of [ 5194-32-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5194-32-1 ]

Product Details of [ 5194-32-1 ]

CAS No. :	5194-32-1	MDL No. :	MFCD08235210
Formula :	C₆H₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NMGIXZFBQPETOK-UHFFFAOYSA-N
M.W :	138.12	Pubchem ID :	13670875
Synonyms :

Calculated chemistry of [ 5194-32-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.96
TPSA :	63.08 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) :	-7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.02
Log Po/w (XLOGP3) :	0.13
Log Po/w (WLOGP) :	0.48
Log Po/w (MLOGP) :	-0.47
Log Po/w (SILICOS-IT) :	0.7
Consensus Log Po/w :	0.37

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.16
Solubility :	9.64 mg/ml ; 0.0698 mol/l
Class :	Very soluble
Log S (Ali) :	-1.01
Solubility :	13.5 mg/ml ; 0.0975 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.38
Solubility :	5.71 mg/ml ; 0.0413 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.15

Safety of [ 5194-32-1 ]

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 [ 5194-32-1 ]

* 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 [ 5194-32-1 ]
Downstream synthetic route of [ 5194-32-1 ]

[ 5194-32-1 ] Synthesis Path-Upstream 1~3

1
[ 2134-38-5 ]
[ 5194-32-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 295 - 305
[2] Patent: EP1557411, 2005, A1, . Location in patent: Page/Page column 16

2
[ 7752-78-5 ]
[ 124-38-9 ]
[ 5194-32-1 ]

Reference： [1] Heterocycles, 1994, vol. 38, # 6, p. 1375 - 1382

3
[ 5194-32-1 ]
[ 2239-83-0 ]

Yield	Reaction Conditions	Operation in experiment
62.6%	at 20℃; for 3 h;	Step 1 (2-methylpyrimidin-5-yl)methanol To a solution of 2-methylpyrimidine-5-carboxylic acid (150 mg, 1.23 mmOl) in ethanol (5 mL) was added sodium borohydride(93 mg, 2.46 mmol). The mixture was stirred at room temperature for 3 h. It was quenched with aqueous HC1 (2 N, 2 mL), extracted with DCM, dried over sodium sulfate, filtered and concentrated give the yellow oil product (2-methylpyrimidin-5-yl)methanol (95 mg, 62.6percent). LCMS MH⁺ 125.
62.6%	With sodium tetrahydroborate In ethanol at 20℃; for 3 h;	To a solution of 2-methylpyrimidine-5-carboxylic acid (150 mg, 1.23 mml) in ethanol (5 mL) was added sodium borohydride (93 mg, 2.46 mmol). The mixture was stirred at room temperature for 3 h. It was quenched with aqueous HCl (2 N, 2 mL), extracted with DCM, dried over sodium sulfate, filtered and concentrated give the yellow oil product (2-methylpyrimidin-5-yl)methanol (95 mg, 62.6percent). LCMS MH⁺ 125.

Reference： [1] Patent: WO2014/143799, 2014, A2, . Location in patent: Page/Page column 387
[2] Patent: US2014/275528, 2014, A1, . Location in patent: Paragraph 0309; 0310

[ 5194-32-1 ] Synthesis Path-Downstream 1~33

1
[ 7752-78-5 ]
[ 124-38-9 ]
[ 5194-32-1 ]

Reference： [1]Heterocycles,1994,vol. 38,p. 1375 - 1382

2
[ 2134-38-5 ]
[ 5194-32-1 ]

Yield	Reaction Conditions	Operation in experiment
		In 30 ml of ethanol and 20 ml of a 1M sodium hydroxide aqueous solution, 2.9 g of <strong>[2134-38-5]ethyl 2-methylpyrimidine-5-carboxylate</strong> was stirred for 2 hours. The solvent was removed by evaporation and an appropriate amount of water and diethyl ether were added thereto, followed by liquid-separating operation. The resulting aqueous layer was made weakly acidic with a 1M hydrochloric acid aqueous solution and then the resulting crystals were collected by filtration, washed with water, and then dried to obtain 1.9 g of the title compound. FABMASS 139 [M+H]+

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 295 - 305
[2]Patent: EP1557411,2005,A1 .Location in patent: Page/Page column 16

4
sodium 2-methylpyrimidine-5-carboxylate [ No CAS ]
[ 5194-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water;	Ethyl 2-methyl-5-pyrimidinecarboxylate (may be prepared as described in Description33) (60.0mg, 0.36mmol) was dissolved in ethanol (3ml), treated with 2M sodium hydroxide solution (0.54ml, 1.0deltamrnol) and the resulting mixture stirred at room temperature for 3 hours. The ethanol was evaporated, water (50ml) added and the solution acidified with 2M HCI solution. Extracted with ethyl acetate (3 x 50ml), dried over magnesium sulphate, filtered and evaporated to afford the product (D34); MS (ES+) m/e 139 [M+H]+.

Reference： [1]Patent: WO2006/97691,2006,A1 .Location in patent: Page/Page column 33

5
[ 5194-32-1 ]
[ 100568-79-4 ]
7,7-Dimethyl-2-(2-methylpyrimidin-5-yl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 10 7,7-Dimethyl-2-(2-methylpyrimidin-5-yl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one Analogously to Example 6, starting from 5.7 g. (30 mmol) 5,6-diamino-3,3-dimethylindolin-2-one and 4.8 g. (35 mmol) <strong>[5194-32-1]2-methylpyrimidine-5-carboxylic acid</strong>, there is obtained the monoamide. Yield: 3.6 g. (39% of theory); m.p. 166-170 C. after recrystallisation from water. The crude product is subsequently cyclised with glacial acetic acid to give the title compound. Yield: 2.3 g. (68.5% of theory); m.p.>350 C.
		EXAMPLE 10 7,7-Dimethyl-2-(2-methylpyrimidin-5-yl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one Analogously to Example 6, starting from 5.7 g. (30 mmol) 5,6-diamino-3,3-dimethylindolin-2-one and 4.8 g. (35 mmol) <strong>[5194-32-1]2-methylpyrimidine-5-carboxylic acid</strong>, there is obtained the monoamide. Yield: 3.6 g. (39% of theory); m.p. 166-170 C. after recrystallisation from water. The crude product is subsequently cyclised with glacial acetic acid to give the title compound. Yield: 2.3 g. (68.5% of theory); m.p. >350 C.

Reference： [1]Patent: US4695567,1987,A
[2]Patent: US4835280,1989,A

6
[ 5194-32-1 ]
[ 1142924-76-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; toluene; at 0 - 20℃; for 2h;	<strong>[5194-32-1]2-Methylpyrimidine-5-carboxylic acid</strong> (44.2 mg, 320 muiotaetaomicron) was suspended in dichloromethane (5 mL), the suspension was cooled to 0-5C (ice bath) and oxalyl chloride (56.9 mg, 39.3 mu, 448 muiotaetaomicron) as well as dimethylformamide (0.308 M in toluene, 51.9 mu, 16 muiotaetaomicron) were added. The mixture was stirred for 2 h at room temperature. Then, it was concentrated in vacuo (40C, 5 mbar) and dried azeotropically by two cycles of addition of toluene (3 mL) followed by concentration in vacuo to afford 2-methylpyrimidine-5-carbonyl chloride as orange oil (50.0 mg, quant.). After that, tert-butyl ((3aS,4R,8R)-4-(5-amino-2-fluorophenyl)-4,7,7-trimethyl-8-oxido- 3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int-16ABp, 80 mg, 188 mumol) was dissolved in dichloromethane (5 mL), the solution cooled to 10C and N,N- diisopropylethylamine (41.4 mg, 56 mu, 320 mumol) was added, followed by a solution of 2- methylpyrimidine-5-carbonyl chloride (vide supra, 50.0 mg, 320 muiotaetaomicron) in dichloromethane (5 mL). The reaction mixture was stirred for 45 min at 10C. Then, methanol (2 mL) was added, the mixture was stirred for 5 min at room temperature and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 40 g, eluting with 2 M ammonia in methanol / dichloromethane, gradient 1:99 to 4:96) to yield, after drying in vacuo (40C, 5 mbar), the title compound as a light yellow solid (48 mg, purity 67% by HPLC, 31% yield). HPLC (method LCMS_gradient) tR = 2.12 min. MS (ES+) m/z 545.5 [M+H] .
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 0.5h;	2-Methyl-5-pyrimidinecarboxylic acid [e.g. available from Chemstep] (72 mg) was dried under vacuum over phosphorous pentoxide for 3 days and was then suspended in dry dichloromethane (1.5 ml) and treated at 20 C. with oxalyl chloride (0.046 ml) and DMF (1 drop). Rapid effervescence occurred and the mixture was stirred at room temperature for 30 mins and then added dropwise to a solution of Intermediate 16 (143 mg) in acetonitrile (3 ml). DIPEA (0.093 ml) was added and the mixture was stirred at room temperature for 1.75 h. The mixture was blown down to dryness and the residue purified by mass directed autoprep HPLC. Relevant fractions were collected and evaporated to dryness. The residue was further purified by SPE cartridge (5 g, aminopropyl) eluting with methanol. Relevant fractions were collected and evaporated to dryness. The residue was further purified by preparative TLC on a silica plate (20 cm×20 cm×1 mm) eluting with 5% methanol in ethyl acetate. The major band was collected, extracted with 20% methanol in chloroform and filtered and the filtrate evaporated to give Example 331 (70 mg) as a yellow solid. LCMS showed MH+=424; TRET=2.21 min.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 0.5h;	Example 331 lambda/-[1 ,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1 H- pyrazoIo[3,4-b]pyridin-5-yl]methyl}-2-methyl-5-pyrimidinecarboxamide2-Methyl-5-pyrimidinecarboxylic acid [e.g. available from Chemstep] (72mg) was dried under vacuum over phosphorous pentoxide for 3 days and was then suspended in dry dichloromethane (1.5ml) and treated at 200C with oxalyl chloride (0.046ml) and DMF (1 drop). Rapid effervescence occurred and the mixture was stirred at room temperature for 30mins and then added dropwise to a solution of Intermediate 16 (143mg) in acetonitrile (3ml). DIPEA (0.093ml) was added and the mixture was stirred at room temperature for 1.75h. The mixture was blown down to dryness and the residue purified by mass directed autoprep HPLC. Relevant fractions were collected and evaporated to dryness. The residue was further purified by SPE cartridge (5g, aminopropyl) eluting with methanol. Relevant fractions were collected and evaporated to dryness. The residue was further purified by preparative TLC on a silica plate (20cm x 20cm x 1 mm) eluting with 5% methanol in ethyl acetate. The major band was collected, extracted with 20% methanol in chloroform and filtered and the filtrate evaporated to give Example 331 (70mg) as a yellow solid. LCMS showed MH+ = 424; TRET = 2.21 min.

Reference： [1]Patent: WO2017/25491,2017,A1 .Location in patent: Page/Page column 72; 73
[2]Patent: US2009/131431,2009,A1 .Location in patent: Page/Page column 146
[3]Patent: WO2007/36733,2007,A1 .Location in patent: Page/Page column 219

7
[ 1238877-60-5 ]
[ 5194-32-1 ]
[ 1238876-30-6 ]

Yield	Reaction Conditions	Operation in experiment
29%		To a stirred solution of <strong>[5194-32-1]2-methylpyrimidine-5-carboxylic acid</strong> (23 mg, 0.17 mmol) in DCM (3 ml) was added HOBt (23 mg, 0.17 mmol) and HBTU (64 mg, 0.17 mmol). After 3 hours, a solution of l-(Azetidin-3-ylcarbonyl)-4-cyclo butyl- 1 ,4-diazepane (48 mg, 0.17 mmol), in DCM (1 ml) was added and the yellow suspension gradually dissolved to give a yellow solution. The reaction mixture was quenched with saturated NaHCO3 (1 ml) and the aqueous layer extracted with DCM (3 x 5 ml). The combined organic layers were dried (MgSO4), filtered and concentrated at reduced pressure. Purification by silica FCC (eluting with 99: 1 to 95:5 gradient of DCM / 2M NH3 in MeOH) gave the title compound (17.4 mg, 29% yield) as pale yellow oil. LCMS data: Calculated MH+ (358); Found 99% (MH+) m/z 358, Rt = 3.05 min (Method D). NMR data: 1H NMR (500 MHz, CHLOROFORM-J) delta ppm 8.89 (2 H, m), 4.77 (1 H, m), 4.36 - 4.44 (2 H, m), 4.27 - 4.34 (1 H, m), 3.58 - 3.72 (3 H, m), 3.33 - 3.38 (2 H, m), 2.85 (1 H, m), 2.77 (3 H, s), 2.46 - 2.52 (2 H, m), 2.37 - 2.43 (2 H, m), 2.02 (2 H, m), 1.87 (1 H, m), 1.74 - 1.84 (3 H, m), 1.58 - 1.70 (2 H, m).

Reference： [1]Patent: WO2010/86403,2010,A1 .Location in patent: Page/Page column 62

8
[ 5194-32-1 ]
[ 126504-86-7 ]

Reference： [1]Patent: WO2014/143799,2014,A2
[2]Patent: US2014/275528,2014,A1

9
[ 5194-32-1 ]
[ 2239-83-0 ]

Yield	Reaction Conditions	Operation in experiment
62.6%	With sodium tetrahydroborate; ethanol; at 20℃; for 3.0h;	Step 1 (2-methylpyrimidin-5-yl)methanol To a solution of 2-methylpyrimidine-5-carboxylic acid (150 mg, 1.23 mmOl) in ethanol (5 mL) was added sodium borohydride(93 mg, 2.46 mmol). The mixture was stirred at room temperature for 3 h. It was quenched with aqueous HC1 (2 N, 2 mL), extracted with DCM, dried over sodium sulfate, filtered and concentrated give the yellow oil product (2-methylpyrimidin-5-yl)methanol (95 mg, 62.6%). LCMS MH+ 125.
62.6%	With sodium tetrahydroborate; In ethanol; at 20℃; for 3.0h;	To a solution of 2-methylpyrimidine-5-carboxylic acid (150 mg, 1.23 mml) in ethanol (5 mL) was added sodium borohydride (93 mg, 2.46 mmol). The mixture was stirred at room temperature for 3 h. It was quenched with aqueous HCl (2 N, 2 mL), extracted with DCM, dried over sodium sulfate, filtered and concentrated give the yellow oil product (2-methylpyrimidin-5-yl)methanol (95 mg, 62.6%). LCMS MH+ 125.

Reference： [1]Patent: WO2014/143799,2014,A2 .Location in patent: Page/Page column 387
[2]Patent: US2014/275528,2014,A1 .Location in patent: Paragraph 0309; 0310

10
[ 5194-32-1 ]
1,3-dimethyl-7-((2-methylpyrimidin-5-yl)methyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione [ No CAS ]

Reference： [1]Patent: US2014/275528,2014,A1

11
tert-butyl 3-[3-(6-aminopyridin-3-yl)phenyl]amino}pyrrolidine-1-carboxylate [ No CAS ]
[ 5194-32-1 ]
C₂₆H₃₀N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2-chloro-1-methyl-pyridinium iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 48h;	Steps 3/4: 2-Chloro-1-methylpyridinium iodide (288 mg, 11.299 mmol,2.0 eq.) and DIPEA (0.2 mL) were added to a stirred solution of tert-butyl-3-[3-(6-aminopyridin-3-yl)phenyl]amino}pyrrolidine-1-carboxylate (200 g,0.565 mmol, 1 .0 eq.) and <strong>[5194-32-1]2-methyl-pyrimidine-5-carboxylic acid</strong> (78 mg,0.565 mmol, 1 .0 eq.) in THF (20 mL) at RT. The reaction mixture was stirredfor 48 hours at RT then diluted with ethyl acetate (100 mL) then washed with water and brine (100 mL each). The organic layer was dried over Na2504 and concentrated under reduced pressure to obtain crude product. This material was purified by preparative HPLC then dissolved in a solution of HCI in dioxane (4N, 50 ml). After stirring for 1 hour at RT, the reactionmixture was concentrated under reduced pressure and the final product was isolated by trituration with pentane to give 2-methyl-N-{5-[3-(pyrrolidin-3- ylamino)phenyl]pyridin-2-yl}pyrimidine-5-carboxamide (55) (40 mg; 17 %).

Reference： [1]Patent: WO2015/127284,2015,A2 .Location in patent: Page/Page column 79

12
[ 5194-32-1 ]
5-bromo-3-fluoro-pyridin-2-ylamine [ No CAS ]
N-(5-bromo-3-fluoropyridin-2-yl)-2-methylpyrimidine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.4%	With pyridine; trichlorophosphate; at 0 - 20℃; for 1h;	Step 3: POd3 (0.4 mL, 4.04 mmol, 3.0 eq.) was added to a stirred solution of <strong>[5194-32-1]2-methylpyrimidine-5-carboxylic acid</strong> (500 mg, 3.68 mmol, 1 .0 eq.) and 5-bromo-3-fluoropyridin-2-amine (700 mg, 3.68 mmol, 1 .0 eq.) in pyridine (10 ml) at 0 C. The reaction mixture was stirred for I h at RT afterwhich time it was poured into ice water. The resulting solid was dried to afford N-(5-bromo-3-fluoropyridi n-2-yl )-2-methyl pyrimidine-5-carboxamide (700 mg; 61.4%)

Reference： [1]Patent: WO2015/127284,2015,A2 .Location in patent: Page/Page column 85

13
[ 33421-40-8 ]
[ 5194-32-1 ]
2-methyl-N-(5-phenylpyridin-2-yl)pyrimidine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%		General procedure: General CouIinQ Procedure 2 HATU (1 .5 eq.) was added to a stirred solution of Carboxylic acid A (1 .0 eq.) and Amine B (1.2 eq.) in DMF (25 mL) at 0 C and, after 30 mm. ofadditional stirring, DIPEA (4.0 eq.) was added in dropwise fashion and the total reaction mixture was stirred at RT for 16 h. After completion of the reaction, ice water was added to the reaction mixture and the precipitated solid was filtered and washed with ethyl acetate (100 ml) and diethyl ether (100 ml) before drying under reduced pressure to obtain pure product.Additional purification by flash chromatography over silica was performed when necessary.

Reference： [1]Patent: WO2015/127284,2015,A2 .Location in patent: Page/Page column 51; 102

14
[ 1072-97-5 ]
[ 5194-32-1 ]
N-(5-bromopyridin-2-yl)-2-methylpyrimidine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.9%	With pyridine; trichlorophosphate; at 0 - 20℃; for 1h;	Step 1: POCI3 (5.30 mL, 56.7 mmol, 3.0 eq.) was added to a stirredsolution of <strong>[5194-32-1]2-methylpyrimidine-5-carboxylic acid</strong> (2.62 g, 18.9 mmol, 1 .0 eq.)and 5-bromopyridin-2-amine (3.00 g, 18.9 mmol, 1.0 eq.) in pyridine (30 mL)at 0 C and the resulting solution was stirred for I h at RT. The reactionmixture was then filtered and the filtrate was diluted with ethyl acetate (100mL) then washed with water and brine (100 mL each). The organic layer was dried over Na2504 and concentrated under reduced pressure to obtain N-(5- bromopyridin-2-yl)-2-methylpyrimidine-5-carboxamide (4.00 g; 71 .9 %).

Reference： [1]Patent: WO2015/127284,2015,A2 .Location in patent: Page/Page column 82

15
5-[5-chloro-3-(4-methylpiperazin-1-yl)phenyl]pyridin-2-amine [ No CAS ]
[ 5194-32-1 ]
N-{5-[3-chloro-5-(4-methylpiperazin-1-yl)phenyl]pyridin-2-yl}-2-methylpyrimidine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27.2%	With pyridine; trichlorophosphate; at 0 - 20℃; for 1h;	General procedure: General CoulinQ Procedure 5 POd3 (3 eq.) was added to a stirred solution of carboxylic acid A (1 .0 eq.) and amine B (1 .0 eq.) in pyridine (25 mL) at 0 C. The reaction mixturewas stirred for I h at RT. The reaction mixture was then filtered and the filtrate was diluted with ethyl acetate (100 mL) then washed with water and brine (100 mL each). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to obtain the crude product, which was then purified by preparative H PLC.

Reference： [1]Patent: WO2015/127284,2015,A2 .Location in patent: Page/Page column 52; 104

16
tert-butyl 4-[3-chloro-5-(5-fluoro-6-aminopyridin-3-yl)phenyl]piperazine-1-carboxylate [ No CAS ]
[ 5194-32-1 ]
N-{5-[3-chloro-5-(4-boc-piperazin-1-yl)phenyl]-3-fluoropyridin-2-yl}-2-methyl pyrimidine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With pyridine; trichlorophosphate; at 0 - 20℃; for 1h;	Step 2: POd3 (0.27 mL, 2.94 mmol, 3.0 eq.) was added to a stirred solution of <strong>[5194-32-1]2-methylpyrimidine-5-carboxylic acid</strong> (136 mg, 0.98 mmol, 1 .0 eq.) and tert-butyl 4-[3-chloro-5-(5-fluoro-6-aminopyridin-3- yl)phenyl]piperazine-1-carboxylate (400 mg, 0.98 mmol, 1.0 eq.) in pyridine (4 ml) at 0 C. The reaction mixture was stirred for I h at RT. The reaction mixture was then filtered and the filtrate was diluted with ethyl acetate (100mL) then washed with water and brine (100 mL each). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to obtain crude product which was purified by preparative HPLC to give pure N-{5-[3-chloro- 5-(4-Boc-piperazin-1 -yl )phenyl]-3-fluoropyridin-2-yl}-2-methyl pyrimidine-5- carboxamide (300 mg; 58%).

Reference： [1]Patent: WO2015/127284,2015,A2 .Location in patent: Page/Page column 76; 77

17
[ 5194-32-1 ]
N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-yl)-2-methylpyrimidine-5-carboxamide [ No CAS ]