[ CAS No. 153286-94-3 ] {[proInfo.proName]}

Name: 153286-94-3|5-Ethynylpyrimidine|98%
Brand: Ambeed
SKU: A287391
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Quality Control of [ 153286-94-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 153286-94-3 ]

CAS No. :	153286-94-3	MDL No. :	MFCD01936255
Formula :	C₆H₄N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GFVQKBROKWSUNG-UHFFFAOYSA-N
M.W :	104.11	Pubchem ID :	1475194
Synonyms :

Calculated chemistry of [ 153286-94-3 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	29.97
TPSA :	25.78 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) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	0.45
Log Po/w (WLOGP) :	0.54
Log Po/w (MLOGP) :	0.18
Log Po/w (SILICOS-IT) :	1.51
Consensus Log Po/w :	0.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.32
Solubility :	4.94 mg/ml ; 0.0474 mol/l
Class :	Very soluble
Log S (Ali) :	-0.56
Solubility :	28.7 mg/ml ; 0.276 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.66
Solubility :	2.26 mg/ml ; 0.0217 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 153286-94-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 153286-94-3 ]

* 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 [ 153286-94-3 ]
Downstream synthetic route of [ 153286-94-3 ]

[ 153286-94-3 ] Synthesis Path-Upstream 1~2

1
[ 216309-28-3 ]
[ 153286-94-3 ]

Reference： [1] Monatshefte fur Chemie, 1998, vol. 129, # 10, p. 1035 - 1048
[2] Organic and biomolecular chemistry, 2003, vol. 1, # 3, p. 498 - 506
[3] Journal of Organic Chemistry, 2007, vol. 72, # 13, p. 4750 - 4755
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3743 - 3748
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3033 - 3047
[6] Organic Letters, 2014, vol. 16, # 17, p. 4524 - 4527

2
[ 584-08-7 ]
[ 216309-28-3 ]
[ 153286-94-3 ]

Reference： [1] Patent: US2008/70931, 2008, A1, . Location in patent: Page/Page column 12

[ 153286-94-3 ] Synthesis Path-Downstream 1~56

1
[ 150878-37-8 ]
[ 153286-94-3 ]
[ 157195-66-9 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2437 - 2444

2
[ 1730-04-7 ]
[ 153286-94-3 ]
[ 216309-08-9 ]

Reference： [1]Monatshefte fur Chemie,1998,vol. 129,p. 1035 - 1048

3
[ 216309-28-3 ]
[ 153286-94-3 ]

Reference： [1]Monatshefte fur Chemie,1998,vol. 129,p. 1035 - 1048
[2]Organic and biomolecular chemistry,2003,vol. 1,p. 498 - 506
[3]Journal of Organic Chemistry,2007,vol. 72,p. 4750 - 4755
[4]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3743 - 3748
[5]Journal of Medicinal Chemistry,2013,vol. 56,p. 3033 - 3047
[6]Organic Letters,2014,vol. 16,p. 4524 - 4527
[7]MedChemComm,2019,vol. 10,p. 263 - 267

4
[ 50-00-0 ]
[ 153286-94-3 ]
[ 626-56-2 ]
5-[(3-methylpiperidin-1-yl)prop-1-ynyl]pyrimidine [ No CAS ]

Reference： [1]Organic and biomolecular chemistry,2003,vol. 1,p. 498 - 506

5
[ 87-82-1 ]
[ 153286-94-3 ]
hexakis(5-pyrimidylethynyl)benzene [ No CAS ]

Reference： [1]Heterocycles,2004,vol. 63,p. 1537 - 1540

6
[ 153286-94-3 ]
[ 780755-05-7 ]
6-pyrimidin-5-yl-biphenyl-3,4-dicarboxylic acid dimethyl ester [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 11449 - 11455

7
[ 4595-59-9 ]
[ 153286-94-3 ]
[ 424838-43-7 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 3486 - 3487

8
[ 584-08-7 ]
[ 216309-28-3 ]
[ 153286-94-3 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 20℃; for 2h;	b) 5-Ethynyl-pyrimidine; Potassium carbonate (7.38 g, 53.4 mmol) was added in one portion to a stirred solution of <strong>[216309-28-3]5-trimethylsilanylethynyl-pyrimidine</strong> (4.71 g, 26.7 mmol) in methanol (10 ml). The reaction mixture was stirred for 2 hours at room temperature then concentrated in vacuo. The residue was suspended in dichloromethane and the inorganic solids were removed by filtration. The filtrate was concentrated in vacuo to remove ca. 95percent of the solvent to afford 5-ethynyl-pyrimidine as a brown oil in crude form. This material was used in the subsequent Sonogashira reaction without further purification.

Reference： [1]Patent: US2008/70931,2008,A1 .Location in patent: Page/Page column 12

9
[ 1012792-65-2 ]
[ 1012792-59-4 ]
[ 153286-94-3 ]
[ 1012792-61-8 ]
[ 1012792-60-7 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; N-ethyl-N,N-diisopropylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenylphosphine on polystyrene; In tetrahydrofuran; at 120℃; for 20h;	d) 6-Pyrimidin-5-yl-ethynyl-5-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester and 6-pyrimidin-5-ylethynyl-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester; A degassed solution of <strong>[153286-94-3]5-ethynyl-pyrimidine</strong> (2.0 mmol) in tetrahydrofuran and N-ethyldiisopropylamine (1:1, 10 ml) was added to a degassed suspension of 2-chloro-5-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester and 2-chloro-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester (45:55, 296 mg, 1.0 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (1:1) (49 mg, 0.06 mmol), polymer supported triphenylphoshine (135 mg, 1.48 mmol/g, 0.2 mmol) and copper(I)iodide (11 mg, 0.06 mmol) in tetrahydrofuran and N-ethyldiisopropylamine (1:1, 5 ml). The reaction mixture was heated at 120° C. for 20 hours under an atmosphere of nitrogen. The reaction mixture was cooled to room temperature and the solids were removed by filtration. The solids were washed with ethyl acetate (100 ml), the organic liquors were combined and washed with saturated aqueous ammonium chloride solution (3.x.50 ml). The organic layer was then dried over MgSO4 and concentrated in vacuo. Purification by flash column chromatography (20percent ethyl acetate/heptane) gave a mixture of 6-pyrimidin-5-ylethynyl-5-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester and 6-pyrimidin-5-ylethynyl-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester as a brown oil in a 1:1 ratio, 330 mg (83percent yield). LC at 215 nm; Rt 2.21: 43percent, m/z (ES+): 384 (M+H) and Rt 2.33: 43percent, m/z (ES+): 398 (M+H).

Reference： [1]Patent: US2008/70931,2008,A1 .Location in patent: Page/Page column 12

10
[ 29162-73-0 ]
[ 153286-94-3 ]
5,10,15,20-tetrakis(4-(5-pyrinidinylethynyl)phenyl)porphyrin [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 4750 - 4755

11
[ 941601-16-7 ]
[ 153286-94-3 ]
4β-{2-(N-acetylamino)-5-[(5-pyrimidyl)ethynyl]benzoyloxy}-1α,14α,16β-trimethoxy-20-ethylaconitane-8,9-diol [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 356 - 360
[2]Doklady Chemistry,2007,vol. 415,p. 181 - 185

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; methanol; at 20℃; for 2h;	General procedure: THF / methanol mixed solution (10 mL, 15.0 mL) of the compound of Reference Example 48 (584 mg) in was added potassium carbonate (843 mg), and stirred at room temperature for 2 hours. After completion of the reaction, and extracted with ethyl acetate by the addition of water. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, vacuum filtered and concentrated, the resulting residue was purified by silica gel column chromatography (n- hexane / ethyl acetate) to give the title compound (324 mg) was obtained.

13
bis(triphenylphosphine)palladium(II) dichloride [ No CAS ]
[ 372080-84-7 ]
[ 153286-94-3 ]
3-cyclopentyl-2-(4-pyrimidin-5-ylethynyl-phenyl)-propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine; In N,N-dimethyl-formamide;	A solution of 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (719 mg, 2.01 mmol) and triethylamine (3 mL, 0.015 mmol) in N,N-dimethylformamide (3 mL) was treated with <strong>[153286-94-3]5-ethynyl-pyrimidine</strong> (230 mg, 2.21 mmol). The resulting reaction mixture was degassed with argon for 10 min and then treated with cooper iodide (92 mg, 0.48 mmol) and bis(triphenylphosphine)palladium (II) chloride (169 mg, 0.24 mmol). The reaction was stirred at 25° C. for 18 h and then heated at 67° C. for 2 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-pyrimidin-5-ylethynyl-phenyl)-propionic acid methyl ester (440 mg, 66percent) as an orange oil: EI-HRMS m/e calcd for C21H22N2O2(M+) 334.1681, found 334.1681.

Reference： [1]Patent: US2001/53851,2001,A1

14
[ 1025054-90-3 ]
[ 153286-94-3 ]
[ 1025052-65-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1804 - 1809

15
[ 36389-82-9 ]
[ 1112-67-0 ]
[ 153286-94-3 ]
(Bu₄N)2[Pt(C₂C₄H₃N₂-5)4] [ No CAS ]

Reference： [1]Inorganic Chemistry,2004,vol. 43,p. 812 - 821

16
[ 892397-82-9 ]
[ 153286-94-3 ]
2,2,5,5-tetramethyl-4-{2-[p-(pyrimidin-5-ylethynyl)phenyl]vinyl}-3-imidazolin-1-oxyl 3-oxide [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 8807 - 8814

17
[ 162379-72-8 ]
[ 153286-94-3 ]
[Pt(4,4'-tBu₂bipy)(CC-(5-pyrimidinyl))2] [ No CAS ]

Reference： [1]Polyhedron,2009,vol. 28,p. 227 - 232

18
silver nitrate [ No CAS ]
[ 153286-94-3 ]
[ 1173936-46-3 ]

Reference： [1]Inorganic Chemistry,2009,vol. 48,p. 6480 - 6489

19
[ 883877-33-6 ]
[ 153286-94-3 ]
[ 1188490-27-8 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 7211 - 7219

20
3-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl) phenyl)benzamide [ No CAS ]
[ 153286-94-3 ]
[ 1314640-65-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3743 - 3748

21
[ 1671-87-0 ]
[ 153286-94-3 ]
3,6-di(2-pyridyl)4-pyrimidylpyridazine [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 8206 - 8212

22
[ 153286-94-3 ]
[ 364369-52-8 ]
3,6-di(2-pyrazinyl)-4-(pyrimidyl)pyridazine [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 8206 - 8212

23
[ 153286-94-3 ]
5-(AgC₂)-pym*3(silver trifluoroacetate)*3H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry,2009,vol. 48,p. 6480 - 6489

24
[ 215313-78-3 ]
[ 153286-94-3 ]
[ 1391870-10-2 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 4329 - 4331

25
[ 153286-94-3 ]
4-(imidazol-1-ylmethyl)-N-(3-halo-4-methyl-phenyl)-3-(trifluoromethyl)benzamide [ No CAS ]
[ 1428445-71-9 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3033 - 3047

26
[ 5633-34-1 ]
[ 153286-94-3 ]
5-(1-propynyl)pyrimidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 10421 - 10426

27
[ 154386-63-7 ]
[ 153286-94-3 ]
[ 1603104-84-2 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 1843 - 1846

28
[ 2675-79-8 ]
[ 153286-94-3 ]
5-[2-(3,4,5-trimethoxyphenyl)ethynyl]pyrimidine [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 10637 - 10640

29
[ 2926-29-6 ]
[ 153286-94-3 ]
3,3,3-trifluoro-1-(pyrimidin-5-yl)propan-1-one [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4524 - 4527

30
[ 60666-28-6 ]
[ 153286-94-3 ]
1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(5-pyrimidinyl)-1H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With copper(II) sulfate; sodium L-ascorbate; In methanol; water;	General procedure: To a stirring solution of 3 (1 eq.) in MeOH (5 vol) was added alkyne(1 eq.) followed by 100 mM aq. CuSO4 (5 mol %) and 100 mM aq. sodium ascorbate (10 mol %). The reaction was diluted with DCM (10 mL). The tan ppt was then collected by filtration. The organic layer filtrate was evaporated to give a crude crystalline solid. The ppt and crystals were combined and purified by MPLC over C18 silica gel (Grace Reveleris X2, A: H2O + 0.1% TFA, B: ACN + 0.1% TFA, 5-30% B). Theeluent was removed by lyophilisation to give a colourless powder (86 mg, 56%). LCMS:Rt = 1.99 min, 99 A% 254 nm, [M + H]+ = 300.8. 1HNMR (600 MHz, DMSO-d6) delta 9.19 (s, 2H), 9.18 (s,1H), 8.70 (s, 1H), 8.07 (s, 1H), 4.94 (dd, J= 6.5, 4.7 Hz, 2H), 4.79 (dd, J =6.5, 4.8 Hz, 2H), 2.00 (s, 3H). 13C NMR (150 MHz, DMSO-d6) delta 157.7, 153.3, 151.3, 140.8, 138.4, 133.3, 124.7, 123.7, 49.1,45.9, 13.0. HRMS calcd for C12H12N8NaO2 [M + Na]+, 323.0975; found, 323.0966.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 96 - 102

31
[ 124854-94-0 ]
[ 153286-94-3 ]
(E)-3-(2-(pyrimidin-5-ylethynyl)phenyl)prop-2-en-1-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15441 - 15450

32
[ 124854-94-0 ]
[ 153286-94-3 ]
(Z)-5-((1H-inden-1-ylidene)methyl)pyrimidine [ No CAS ]
(E)-5-((1H-inden-1-ylidene)methyl)pyrimidine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15441 - 15450

33
(S)-2-(1-((6-amino-5-iodopyrimidin-4-yl)amino)ethyl)-3-cyclopropyl-5-(1-methyl-1H-pyrazole-4-yl)quinazoline-4(3H)-one [ No CAS ]
[ 153286-94-3 ]
(S)-2-(1-((6-amino-5-(pyrimidin-5-ylethynyl)pyrimidin-4-yl)amino)ethyl)-3-cyclopropyl-5-( 1-methyl-1H-pyrazol-4-yl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.5%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 90℃; for 17h;Inert atmosphere;	To a mixture of (iS)-2-(l-((6-am.ino-5-iodopyrimidin-4-y].)amino)ethyl)-3- cyclopropyl-5-(I -methyl- lH-pyrazol-4-yl)qumazolin-4(3H)-one (40.0 mg, 0.08 mmol) and 5- ethynylpyrimidine (12.0 mg, 0.12 mmol ) in DMF (1 .5 mL) was added Pd(PPh3)2Cl2 (1 1.0 mg, 0.02 mmol), Cul (2.0 mg, 0.01 mmol) and triethylamine (0.05 mL, 0.4 mmol), then the mixture was purged with nitrogen and heated at 90 C under N2 atmosphere for 17 hours. The mixture was cooled to rt, then concentrated in vacuo, and the residue was purified by a flash silica gel column chromatography (DCM/MeOH (v/v) =20/1) to give the title compound as an off-white solid (9.0 mg, yield 23.5%). MS (ESI, pos. ion) m/z: 505.4 [M+H]+; FontWeight="Bold" FontSize="10" H NMR (600 MHz, CDCb) delta (ppm): 9.23 (s, 1 H), 8.97 (s, 2 H), 8.22 (s, 1 H), 7.67 (s, 1 H), 7.66-7.65 (t, J= 7.7 Hz, 1 H), 7.63 (s, 1 H), 7.43-7.42 (dd, J = 8.1, 1.1 Hz, 1 H), 7.35-7.33 (dd, J = 7.5, 1.2 Hz, 1 H), 6.86-6.85 (d, J = 7.8 Hz, 1 H), 6.22-6.18 (dq, J = 13.4, 6.7 Hz, 1 H), 5.37 (s, 2 H), 4.00 (s, 3 H), 3.03-2.99 (m, 1 H), 1.65-1.64 (d, J = 6.6 Hz, 3 H), 1.44-1.42 (m, 2 H), 1.06- 1.01 (m, 1 H), 0.87-0.86 (m, 1 H).
23.5%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 90℃; for 17h;Inert atmosphere;	Compound (S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-3-cyclopropyl-5-(1-yl-1H-pyrazole- 4-yl)quinazoline-4(3H)-one (40.0 mg, 0.08 mmol) and <strong>[153286-94-3]5-ethynylpyrimidine</strong> (12.0 mg, 0.12 mmol) were dissolved in DMF (1.5 mL).Then, Pd(PPh3)2Cl2 (11.0 mg, 0.02 mmol), cuprous iodide (2.0 mg, 0.01 mmol) and triethylamine (0.05 mL, 0.4 mmol) were added to the reaction mixture.The resulting mixture was stirred at 90 C for 17 hours under nitrogen.Then cooled to room temperature and concentrated under reduced pressure.The residue was purified by flash column chromatography eluting elutThe title compound was obtained as a white solid (yield: 9.0mg, 23.5%).

Reference： [1]Patent: WO2015/175579,2015,A1 .Location in patent: Paragraph 369
[2]Patent: CN105130966,2019,B .Location in patent: Paragraph 0530; 0623-0624; 0636-0639

34
(S)-3-(1-((6-amino-5-iodopyrimidin-4-yl)amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one [ No CAS ]
[ 153286-94-3 ]
(S)-3-(1-((6-amino-5-(pyrimidin-5-ylethynyl)pyrimidin-4-yl)amino)ethyl)-8-chloro-2-phenylisoquinoline-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41.3%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 75℃; for 5h;	To a mixture of (5)-3-(l-((6-amino-5-iodopyrimidin-4-yl)amino)ethyl)-8-ehloro- 2-phenylisoquinoim-l(2//)-one (50.8 mg, 0.0981 mmol), Cul (2.2 mg, 0.012 mmol), and Pd(PPh3)2Cl2 (14.3 mg, 0.020 mmol) in anhydrous DMF (2 ml) was added <strong>[153286-94-3]5-ethynylpyrimidine</strong> (31.6 mg, 0.304 mmol), and followed by the addition of tri ethyl amine (0.05 mL, 0.40 mmol). The resulted solution was heated to 75 C and stirred further for 5 hours, then cooled to rt, and quenched with water (15 mL), The resulted mixture was extracted with DCM (30 mL x 3), and the combined organic phases were washed with saturated brine (20 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) :::: 100/5) to give the title compound as a yellowish solid (30 mg, yield 41.3%). MS (ESI, pos. ion) m/z: 494.2 [M+H]+; FontWeight="Bold" FontSize="10" H NMR (600 MHz, OMSO-de) delta (ppm): 9.12 (d, J = 6.4 Hz, 2H), 7.89 (s, 1H), 7.60 (d, J = 3.9 Hz, 2H), 7.55-7.32 (m, 7H), 6.88 (d, J = 6.7 Hz, 2H), 6.75 (s, 1H), 4.75-4.61 (m, 1H), 1.33 (d, 3H).
41.3%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 75℃; for 5h;	To the compound (S)-3-(1-((6-amino-5-iodopyrimidin-4-yl)amino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one (50.8 mg, 0.0981 mmol),Cuprous iodide (2.2 mg, 0.012 mmol) and Pd(PPh3)2Cl2 (14.3 mg, 0.020 mmol)In anhydrous DMF (2mL)The mixture in the middle was added with <strong>[153286-94-3]5-ethynylpyrimidine</strong> (31.6 mg, 0.304 mmol)And triethylamine (0.05 mL, 0.40 mmol).The resulting solution was heated to 75 C and stirring was continued for 5 hours.Cool to room temperature,The reaction was quenched by the addition of water (15 mL).The resulting mixture was extracted with dichloromethane (30 mL x 3).The combined organic phases were washed with brine (20 mL).Dry over anhydrous sodium sulfate and concentrate under reduced pressure.The residue obtained was subjected to silica gel column chromatography (DCM/MeOH (v/v)=100/5The title compound was obtained as a pale yellow solid (30 mg, 41.3%).

Reference： [1]Patent: WO2015/175579,2015,A1 .Location in patent: Paragraph 378
[2]Patent: CN105130966,2019,B .Location in patent: Paragraph 0527; 0678-0682

35
[ 1620056-47-4 ]
[ 153286-94-3 ]
(S)-tert-butyl (1-(3-bromo-6-(pyimidin-5-ylethynyl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine; In tetrahydrofuran; at 40℃; for 2h;Inert atmosphere;	[0242] Synthesis of (S)-tert-butyl (l-(3-bromo-6 pyimidin-5-ylemynyl)pyridm-2-yl)-2-(3,5- difluorophenyl)ethyl)carbamate (1G): (S)-tert-butyl (l-(3,6-dibromopyridin-2-yl)-2-(3,5- difluorophenyl)ethyl)carbamate (1G, 50 mg, 0.1 mmol) and 5-emynylpyrimidine (11.5 mg, 0.11 mmol) in THF (0.2 mL) was degassed and purged with argon. To it was added TEA (0.05 mL), Pd(PPh3)2Cl2(7 mg, 0.01 mmol) and Cul (2 mg, 0.01 mmol). The reaction was stirred for 2 hr at 40 °C and then cooled to ambient temperature. The reaction mixture was partitioned between EtOAc and 0 (plus 0.1 mL of ammonia). The organics were separated, dried, and removed in vacuo. The residue purified by column chromatography on silica to provide the title compound. MS (m/z) 516.66 [M+H]+.

Reference： [1]Patent: WO2016/33243,2016,A1 .Location in patent: Paragraph 0242

36
(S)-2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)-N-(2-(3,5-difluorophenyl)-1-(2-(methylthio)-5-(3-oxoisoindolin-5-yl)pyrimidin-4-yl)ethyl)acetamide [ No CAS ]
[ 153286-94-3 ]
C₃₆H₂₄F₈N₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 150℃; for 0.5h;Microwave irradiation;	[0269] Synthesis of (S)-2-(3 difluoromemyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro- 1H- indazol-1-yl)-N-(2^3,5-difluoropteoxoisomdolin-5-yl)pyrimidm^-yl)ethyl)acetamide (7H): To a mixture of Cul (2 mg, 0.01 mmol), [Pd(dppf)C.2] (4 mg, 0.005 mmol), 5-emynylpyrimidine (10.5 mg, 0.1 mmol) and compound 7G (35 mg, 0.05 mmol) was added THF (0.5 mL) and Et3N (0.04 mL, 0.03 mmol). The reaction mixture was heated in a microwave at 150 °C for 30 min. After cooled to room temperature it was diluted with EtOAc. To it was added Si-Thiol (130 mg, 1.37 mmol/g) and the mixture was stirred at 40 °C for 1 hour. Then it was filtered and the filtrate was washed with 10percent aq NH4OH , 0 and brine. The organic layer was dried over MgS04, filtered, concentrated and purified by reverse phase HPLC to afford the title product. NMR (400 MHz, Methanol-d4): delta 9.22 (s), 9.08 (d), 8.65 (s), 7.70 - 7.59 (m), 7.44 (d), 6.98 - 6.59 (m), 6.38 (d), 5.47 (q), 5.06 (s), 4.51 (s), 3.09 (d), 2.54 - 2.45 (m). MS (m/z) 752.97 [M+H]+...

Reference： [1]Patent: WO2016/33243,2016,A1 .Location in patent: Paragraph 0269

37
[ 688-73-3 ]
[ 153286-94-3 ]
1-(5-pyrimidyl)-1-tributylstannyl-ethene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20℃; for 36h;Inert atmosphere;	General procedure: To a solution of 3 (1.60 g, 6.32 mmol) in THF (30 mL) under N2 was added PdCl2(PPh3)2 (0.44 g, 0.63 mmol) and tributyltin hydride (2.76 g, 9.48 mmol). The resulting dark brown mixture was stirred at ambient temperature under N2 for 24 h. The mixture was diluted with EtOAc (30 mL) and washed with H2O (3*30 mL) and brine (30 mL). The organic layer was dried (MgSO4), filtered, at the solvent was removed under reduced pressure. The residue was purified by chromatography (EtOAc/hexane, 1:19).

Reference： [1]Tetrahedron,2016,vol. 72,p. 4214 - 4221

38
[ 153286-94-3 ]
1-(5-benzyloxy-2-nitrophenyl)-1-(5-pyrimidyl)ethene [ No CAS ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 4214 - 4221

39
[ 153286-94-3 ]
5-benzyloxy-3-(5-pyrimidyl)indole [ No CAS ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 4214 - 4221

40
[ 153286-94-3 ]
hyrtinadine B [ No CAS ]

Reference： [1]Tetrahedron,2016,vol. 72,p. 4214 - 4221

41
C₃₀H₄₂BrN₃O₆S [ No CAS ]
[ 153286-94-3 ]
C₃₆H₄₅N₅O₆S [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 944 - 949

42
C₂₄H₂₆BrNO₅ [ No CAS ]
[ 153286-94-3 ]
C₃₀H₂₉N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere;	General procedure: Scheme 6-5: In Step 1 the appropriately substituted indole is acylated as known in the art. In Step 2 the appropriately substituted heterocycle is subjected to a bromide species of the appropriate linker to afford the appropriately protected species. In Step 3 the appropriately substituted aryl bromide is subjected to a terminal alkyne as known in the art to afford an internal alkyne. In Step 4 the appropriately substituted para-methoxybenzyl alcohol is deprotected in the presence of CAN to afford a free alcohol. In Step 5 the appropriately substituted phenol is subjected to a sulfonic anhydride to afford a leaving group. In Step 6 the appropriately substituted aryl species is converted to a boronic acid as known in the art. In Step 7 the appropriately substituted boronic acid is subjected to copper bromide to afford an aryl bromide species. In an alternative embodiment this synthetic protocol can simply be applied to other indole isomers to afford substituents on alternative positions.

Reference： [1]Patent: WO2017/35415,2017,A1 .Location in patent: Paragraph 0566; 0628; 0629

43
C₂₃H₂₄BrNO₄ [ No CAS ]
[ 153286-94-3 ]
C₂₉H₂₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere;	General procedure: Scheme 6-5: In Step 1 the appropriately substituted indole is acylated as known in the art. In Step 2 the appropriately substituted heterocycle is subjected to a bromide species of the appropriate linker to afford the appropriately protected species. In Step 3 the appropriately substituted aryl bromide is subjected to a terminal alkyne as known in the art to afford an internal alkyne. In Step 4 the appropriately substituted para-methoxybenzyl alcohol is deprotected in the presence of CAN to afford a free alcohol. In Step 5 the appropriately substituted phenol is subjected to a sulfonic anhydride to afford a leaving group. In Step 6 the appropriately substituted aryl species is converted to a boronic acid as known in the art. In Step 7 the appropriately substituted boronic acid is subjected to copper bromide to afford an aryl bromide species. In an alternative embodiment this synthetic protocol can simply be applied to other indole isomers to afford substituents on alternative positions.

Reference： [1]Patent: WO2017/35415,2017,A1 .Location in patent: Paragraph 0566; 0628; 0629

44
[ 153286-94-3 ]
C₆H₆N₄O₂ [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6240 - 6243

45
[ 153286-94-3 ]
5-(1-azidovinyl)pyrimidine [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6240 - 6243

46
14-(2-azidoacetamido)dehydroabietic acid methyl ester [ No CAS ]
[ 153286-94-3 ]
C₂₉H₃₆N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1%	With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In water; tert-butyl alcohol;Heating;	General procedure: A solution of the azide 87 (0.1 mmol), the alkyne (0.12 mmol), 1 M aq CuSO4·5H2O (0.02 mmol) and 1 M aq. sodium ascorbate (0.02 mmol) in a t-BuOH-H2O 1:1 mixture (3.0 mL) was heated at 50 °C until TLC showed no traces of the starting azide. The solvent was removed under reduced pressure, the residue was dispersed in EtOAc (10 mL) and the solution was washed with H2O, dried over MgSO4, concentrated and purified by chromatography on silica gel to give the target analogues.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 5382 - 5386

47
[ 122775-34-2 ]
[ 153286-94-3 ]
3-(pyridin-5-ethynyl)-chromone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 8h;Inert atmosphere;	3-Iodochromone (14.3 g, 52.3 mmol, 1 eq),5-ethynylpyridine (6.6 g, 63.1 mmol, 1.2 eq),Dichlorobis(triphenyl)phosphorus palladium (369 mg, 0.52 mmol, 0.01 eq)withCopper iodide (200 mg, 1.05 mmol, 0.02 eq) was dissolved in 100 ml of acetonitrile.Under nitrogen protection, N,N-diisopropylethylamine (DIPEA, 36.6 ml, 210.3 mmol, 4 eq) was added dropwise.After 8 hours at room temperature, the reaction was completed.Dry organic solvents,Column chromatography3-(Pyridin-5-ethynyl)-chromone(Compound 4),

Reference： [1]Patent: CN104945389,2018,B .Location in patent: Paragraph 0035; 0065; 0068

48
C₂₇H₃₄N₃O₁₀Pol [ No CAS ]
[ 153286-94-3 ]
[ 333366-32-8 ]
C₂₁H₂₇N₉O₆ [ No CAS ]

Reference： [1]ACS Chemical Biology,2018,vol. 13,p. 2542 - 2550

49
[ 18523-48-3 ]
C₂₇H₃₄N₃O₁₀Pol [ No CAS ]
[ 153286-94-3 ]
C₁₇H₁₈N₈O₆ [ No CAS ]

Reference： [1]ACS Chemical Biology,2018,vol. 13,p. 2542 - 2550

50
[ 18523-48-3 ]
C₂₇H₃₄N₃O₁₀Pol [ No CAS ]
[ 71989-26-9 ]
[ 153286-94-3 ]
C₂₃H₃₀N₁₀O₇ [ No CAS ]

Reference： [1]ACS Chemical Biology,2018,vol. 13,p. 2542 - 2550

51
[ 18523-48-3 ]
C₂₇H₃₄N₃O₁₀Pol [ No CAS ]
[ 71989-18-9 ]
[ 153286-94-3 ]
C₂₂H₂₅N₉O₉ [ No CAS ]

Reference： [1]ACS Chemical Biology,2018,vol. 13,p. 2542 - 2550

52
dineopentyl 5-Bromobenzene-1,3-disulfonate [ No CAS ]
[ 153286-94-3 ]
dineopentyl 5-(5-pyrimidylethynyl)benzene-1,3-disulfonate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 6499 - 6506

53
[ 14248-15-8 ]
[ 153286-94-3 ]
neopentyl 4-(5-pyrimidylethynyl)benzenesulfonate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 6499 - 6506

54
[ 14248-15-8 ]
[ 153286-94-3 ]
4-(5-pyrimidylethynyl)benzenesulfonic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 6499 - 6506

55
[ 677313-80-3 ]
[ 153286-94-3 ]
3-(pyrimidin-5-yl)-2H-benzo[g]chromen-2-one [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 5151 - 5154

56
N-((3-(4-azido-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide [ No CAS ]
[ 153286-94-3 ]
(S)-N-((3-(3-fluoro-4-(4-(pyrimidin-5-yl)-1H-1,2,3-triazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 5886 - 5889

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Physical hazards
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H200	Unstable explosive
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H202	Explosive; severe projection hazard
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H312	Harmful in contact with skin
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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
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Code	Phrase
H400	Very toxic to aquatic life
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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. 153286-94-3 ] {[proInfo.proName]}

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[ 153286-94-3 ] Synthesis Path-Upstream 1~2

[ 153286-94-3 ] Synthesis Path-Downstream 1~56

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Alkynes

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Pyrimidines

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