50840-23-8|5-Methylpyrimidin-2-amine| Ambeed

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Quality Control of [ 50840-23-8 ] Purity: 98% SDS Specification

COA

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Product Details of [ 50840-23-8 ]

CAS No. :	50840-23-8
Formula :	C₅H₇N₃
M.W :	109.13
SMILES Code :	NC1=NC=C(C)C=N1
MDL No. :	MFCD00463477
InChI Key :	MHZNCOBCMWBPPM-UHFFFAOYSA-N
Pubchem ID :	12999933

Safety of [ 50840-23-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 50840-23-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	31.4
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	51.8 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.16
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.22
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.38
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.31
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.69
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.43

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.21
Solubility	6.73 mg/ml ; 0.0616 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.87
Solubility	14.8 mg/ml ; 0.136 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.62
Solubility	2.64 mg/ml ; 0.0242 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.81 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.23

Application In Synthesis of [ 50840-23-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 50840-23-8 ]

[ 50840-23-8 ] Synthesis Path-Downstream 1~35

1
[ 50840-23-8 ]
[ 121-60-8 ]
[ 21415-17-8 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 3028.

2
[ 22536-61-4 ]
[ 50840-23-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With ammonia; In ethanol; water; at 200℃; for 4h;Sealed tube;	Step 1 : To a solution of compound 184 (10.0 g, 77.79 mmol) in IMS (100 ml.) was added aqueous ammonia (35%, 100 ml). The reaction mixture was transferred to a sealed bomb and heated at 200 C for 4 h. The reaction mixture was allowed to cool to room temperature and was concentrated to remove most of the solvent and water (25 ml.) added. The solid obtained was filtered and dried under vacuum to give the desired compound 185 as off-white solid (7.85 g, 92% yield).1H NMR (400 MHz, DMSO-d6) delta 8.06 (s, 2H), 6.30 (s, 2H), 2.03 (s, 3H). LCMS m/z 1 10 [M+H]+.
	With ammonium hydroxide; at 85℃; for 18h;Sealed tube;	A mixture of 2-chloro-5-methylpyrimidine (1 g, 7.78 mmol) and ammonium hydroxide (18.26 mL, 469 mmol) was heated at 85 C in a sealed tube for 18 h. The mixture was cooled to rt and and then ice/water bath, and filtered. The white filter cake was washed with hexanes and suction dried.LCMS (method C ) tR,0.33 min., MH+ = 110.2

References: [1]Patent: WO2013/132376,2013,A1 .Location in patent: Page/Page column 205.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.
[3]Chemische Berichte,1905,vol. 38,p. 3397.
[4]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1261 - 1266.

3
[ 7153-13-1 ]
[ 50840-23-8 ]

References: [1]Chemische Berichte,1905,vol. 38,p. 3397.

4
[ 50-01-1 ]
[ 42588-57-8 ]
[ 50840-23-8 ]

References: [1]Journal of the American Chemical Society,1990,vol. 112,p. 7736 - 7742.

5
[ 50840-23-8 ]
[ 6541-19-1 ]
8-methyl-1,6b,10,11-tetraazabenzo[a]fluorene-5,6-dione [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 168 - 174.

6
[ 50840-23-8 ]
[ 599-88-2 ]

References: [1]Journal of the American Chemical Society,1941,vol. 63,p. 3028.

7
[ 1780-36-5 ]
[ 50840-23-8 ]

References: [1]Chemische Berichte,1905,vol. 38,p. 3397.

8
[ 50840-23-8 ]
[ 929568-22-9 ]
S-6-methoxy-4-(5-methylpyrimidin-2-ylamino)-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With caesium carbonate;palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 150℃; for 1h;Irradiation;	9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (87mg, 0.15mmol) and palladium (II) acetate (21mg, 0.09mmol) were added under nitrogen to a deoxygenated suspension of S- 4-chloro-6-methoxy-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-l-yl}pyrimidine (358mg, lmmol), <strong>[50840-23-8]2-amino-5-methylpyrimidine</strong> (131mg, 1.2mmol) and cesium carbonate (489mg, 1.5mmol) in anhydrous 1,4-dioxane (5ml). The mixture was heated at 1500C in a sealed vessel under microwave irradiation for 1 hour. The mixture was allowed to cool, insoluble material was removed by filtration and the volatiles removed from the filtrate by evaporation. The residue was purified by column chromatography on silica gel eluting with EtOAc / isohexane (20:80 increasing in polarity to 50:50) to give the title compound (136mg, 32%); NMR (500.13 MHz, 373K) 2.10 (IH, s), 2.15 (2H, d), 2.21 (3H, s), 3.77-3.78 (2H, m), 3.76- 3.80 (3H, m), 5.46-5.48 (IH, m), 6.79 (IH, s), 6.95 (IH, s), 7.44-7.47 (IH, m), 7.91-7.93 (IH, m), 7.96 (IH, t), 8.42 (2H, s), 8.62 (IH, s), 8.66-8.68 (IH, m); m/z 431 [MH]+.

References: [1]Patent: WO2007/31745,2007,A1 .Location in patent: Page/Page column 103.

9
[ 50840-23-8 ]
N-{trans-3-[(5-cyano-6-methylpyridin-2-yl)oxy]-2,2,4,4-tetramethylcyclobutyl}-6-methylimidazo[1,2-a]pyrimidine-3-carboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7705 - 7712.

10
[ 209959-33-1 ]
[ 544-97-8 ]
[ 50840-23-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere;	Step B: A mixture of 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (3.0 g, 8.0 mmol), dimethylzinc (1.2 M x 8.0 mL, 9.6 mmol) and [Iota , - bis(diphenylphosphino)ferrocene]dichloropalladium(II) (130 mg, 0.16 mmol) in 1 ,4-dioxane (30 mL) was stirred at 1 10 C for 16 h under Argon. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated NH4C1, water and brine. The organic layer was dried over NaS04, concentrated and purified by silica gel column chromatography (0-35% EtOAc in hexanes) to give a white solid, which was dissolved in trifluoroacetic acid (5.0 mL). After 5 min, the solvent was removed and the residue was partitioned between ethyl acetate and an aqueous saturated NaHC03 solution. The organic layer was dried over NaS04, filtered and concentrated to give the title compound (0.7 g, 80%>) as a white solid. MS m/z 110.1 [M+H]+.
80%		Step B: A mixture of 2-[bis(tert-butoxycarbonyl)amino]-5-bromopyrimidine (3.0 g, 8.0 mmol), dimethylzinc (1.2 M×8.0 mL, 9.6 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (130 mg, 0.16 mmol) in 1,4-dioxane (30 mL) was stirred at 110 C. for 16 h under Argon. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated NH4Cl, water and brine. The organic layer was dried over NaSO4, concentrated and purified by silica gel column chromatography (0-35% EtOAc in hexanes) to give a white solid, which was dissolved in trifluoroacetic acid (5.0 mL). After 5 min, the solvent was removed and the residue was partitioned between ethyl acetate and an aqueous saturated NaHCO3 solution. The organic layer was dried over NaSO4, filtered and concentrated to give the title compound (0.7 g, 80%) as a white solid. MS m/z 110.1 [M+H]+.

References: [1]Patent: WO2013/101974,2013,A1 .Location in patent: Paragraph 00816; 00818.
[2]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 371.

11
[ 50840-23-8 ]
3-bromo-2-(chloromethyl)-6-methylimidazo[1,2-a]pyrimidine [ No CAS ]

References: [1]Patent: WO2013/132376,2013,A1 .
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

12
[ 50840-23-8 ]
1-(3-bromo-6-methylimidazo[1,2-a]pyrimidin-2-yl)-N-methylmethanamine [ No CAS ]

References: [1]Patent: WO2013/132376,2013,A1 .
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

13
[ 50840-23-8 ]
tert-butyl((3-bromo-6-methylimidazo[1,2-a]pyrimidin-2-yl)methyl)(methyl)carbamate [ No CAS ]

References: [1]Patent: WO2013/132376,2013,A1 .
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

14
[ 50840-23-8 ]
methyl 2-[(1R)-1-({3-[bis(tert-butoxycarbonyl)-amino]-6-(2-[(tert-butoxycarbonyl)methylamino]methyl}-6-cyanoimidazo[1,2-a]pyridin-3-yl)pyrazin-2-yl}oxy)ethyl]-4-fluorobenzoate [ No CAS ]

References: [1]Patent: WO2013/132376,2013,A1 .
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

15
[ 50840-23-8 ]
C₂₃H₂₃FN₆O₃ [ No CAS ]

References: [1]Patent: WO2013/132376,2013,A1 .
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

16
[ 50840-23-8 ]
(5R)-8-amino-3-fluoro-5,14,19-trimethyl-18,19-dihydro-7,11-(metheno)pyrimido[2′,1′:2,3]imidazo[4,5-h][2,5,11]benzoxadiazacyclotetradecin-20(5H)-one [ No CAS ]

References: [1]Patent: WO2013/132376,2013,A1 .
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

17
[ 50840-23-8 ]
N-methyl-1-(6-methylimidazo[1,2-a]pyrimidin-2-yl)methanamine [ No CAS ]

References: [1]Patent: WO2013/132376,2013,A1 .

18
[ 50840-23-8 ]
[ 534-07-6 ]
2-(chloromethyl)-6-methylimidazo[1,2-a]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	In tetrahydrofuran; at 90℃; for 72h;Molecular sieve;	Step 2: The reaction was done in two batches using 1 g and 9.36 g of compound 185 and the crude material obtained from both batches was combined for purification. To a slurry of compound 185 (9.36 g, 85.82 mmol) in dry THF (250 mL) was added dichloroacetone (21 .80 g, 171.64 mmol) and 4A molecular sieves (25 g). The reaction mixture was heated at 90 C for 3 days, then the reaction mixture was concentrated and the resulting residue dissolved in water (200 mL). The solution was treated with solid K2C03 (10 g) and stirred for 10 min before extraction with ethyl acetate (3 x 400 mL). The combined ethyl acetate extracts were washed with brine (100 mL) and concentrated to give the crude product as thick brown oil. The aqueous phase was subjected to liquid-liquid extraction with DCM (500 mL) and the resulting product obtained was combined with the crude oil obtained from the ethyl acetate extractions for purification. Purification by silica gel column chromatography using 0.5% - 1 % MeOH in DCM furnished compound 186 as off-white solid (4.2 g, 24% yield).1 H NMR (400 MHz, Chloroform-d) delta 8.44 (d, J = 2.4 Hz, 1 H), 8.23 (dd, J = 2.4, 1 .2 Hz, 1 H), 7.56 (d, J = 0.8 Hz, 1 H), 4.79 (d, J = 0.8 Hz, 2H), 2.37 (d, J = 1.1 Hz, 3H). LCMS m/z 182 [M+H]+.

References: [1]Patent: WO2013/132376,2013,A1 .Location in patent: Page/Page column 205.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

19
[ 1780-31-0 ]
[ 50840-23-8 ]

References: [1]Patent: WO2013/132376,2013,A1 .
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

20
[ 50840-23-8 ]
[ 1335052-44-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3493 - 3498.

21
[ 50840-23-8 ]
[ 1300031-42-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3493 - 3498.

22
[ 50840-23-8 ]
[ 84911-18-2 ]
[ 1335054-73-3 ]

Yield	Reaction Conditions	Operation in experiment
23%	With sodium hydrogencarbonate; In 1,2-dimethoxyethane; for 36h;Inert atmosphere; Reflux;	2-Amino-5-methylpyrimidine (1.0 g, 8.9 mmol), ethyl-2-bromoacetoacetate(2.3 g, 10.7 mmol) and sodium bicarbonate (1.1 g, 13.3 mmol) were dissolved in 25 mL of 1,2-dimethoxyethane (DME) and heated for 36 h at reflux. The reaction mixture was filtered; solids were collected and washed with CH2Cl2. The filtrate was concentrated in vacuo and the residue was dissolved in CH2Cl2 and washed with 5% acetic acid solution (2x) and brine. The organic phase was collected, dried over Na2SO4, filtered and then concentrated in vacuo. Crude material obtained was purified by silica gel column chromatography with a 25% ethyl acetate : CH2Cl2 solvent system to give 0.457 g (23%) of ethyl 2,6-dimethylimidazo[1,2-a]pyrimidine-3-carboxylate as a light solid. 1H NMR (300 MHz, CDCl3) delta 9.37 (dd, J = 2.4, 1.1 Hz, 1H), 8.53 (d, J = 2.4 Hz, 1H), 2.75 (s, 3H), 4.41 (q, J = 7.1, 7.1, 7.1 Hz, 2H), 2.40 (s, 3H) 1.44 (t, J = 7.1, 7.1 Hz, 3H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3493 - 3498.

23
[ 50840-23-8 ]
C₃₈H₄₇FN₆O₉ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4720 - 4744.

24
[ 50840-23-8 ]
C₁₈H₁₇N₃O₂ [ No CAS ]
5-methyl-N-(5-methylpyrimidin-2-yl)-4-[4-(1H-pyrazol-1-yl)benzyl]pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3. Compound C24 was converted to its methyl ester via treatment with hydrogen chloride in methanol at 60 C. 5-Methylpyrimidin-2-amine and trimethylaluminum were combined in toluene and tetrahydrofuran, and heated at 30 C for 16 hours. The methyl ester was then added, and the reaction mixture was heated at 80 o to provide the product.

References: [1]Patent: WO2016/9297,2016,A1 .Location in patent: Page/Page column 119; 125; 126.

25
[ 50840-23-8 ]
[ 1476847-52-5 ]
2-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-6-methylimidazo[1,2-a]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.4%	In isopropyl alcohol; at 20 - 80℃; for 40h;	In an 80 mE high pressure vessel under nitrogen,mixture of <strong>[50840-23-8]5-methylpyrimidin-2-amine</strong> (0.245 g, 2.245 mmol) and 1 -(4-(benzyloxy)-6-methoxybenzothran-2-yl)-2- bromoethanone (0.599 g, 1.596 mmol) in 2-propanol (16 mE) was stirred at room temperature for 16 h and a further 24 h at 80 C. The cooled mixture was diluted with dichloromethane and the organic solution was washed once with saturated aqueous sodium bicarbonate, once with brine and finally it was dried over anhydrous sodium sulfate andconcentrated in vacuo. The residue was purified on the ISCO using a 40 g Innoflash column (Hexane/EtOAc) and the solid obtained was triturated with methanol to give2-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-6-methylimi- dazo[1,2-a]pyrimidine (0.378 mg, 61.4%) as a beige solid. EC (Analytical Method A): 2.117 mm; (Analytical Method B): 2.3 14 mi HRMS (ESI): calcd for C23H2QN303 [M+H] mlz 386.1499; found 386.1488. ?H NMR (400 MHz,DMSO-d5) oe 8.79 (dd, J=1.2, 2.3 Hz, 1H), 8.46 (d, J=2.3 Hz,1H), 8.19 (s, 1H), 7.56-7.50 (m, 2H), 7.46-7.39 (m, 2H),7.38- 7.32 (m, 1H), 7.24 (d, J=0.8 Hz, 1H), 6.90-6.87 (m,1H), 6.55 (d, J=2.0 Hz, 1H), 5.28 (s, 2H), 3.81 (s, 3H), 2.323H).

References: [1]Patent: US9598419,2017,B1 .Location in patent: Page/Page column 63; 64.

26
[ 50840-23-8 ]
6-methoxy-2-(6-methylimidazo[1,2-a]pyrimidin-2-yl)benzofuran-4-ol [ No CAS ]

References: [1]Patent: US9598419,2017,B1 .

27
[ 50840-23-8 ]
4-(((6-methoxy-2-(6-methylimidazo[1,2-a]pyrimidin-2-yl)benzofuran-4-yl)oxy)methyl)-2-phenylthiazole [ No CAS ]

References: [1]Patent: US9598419,2017,B1 .

28
[ 50840-23-8 ]
4-(4-(((6-methoxy-2-(6-methylimidazo[1,2-a]pyrimidin-2-yl)benzofuran-4-yl)oxy)methyl)thiazol-2-yl)-N,N-dimethylbenzamide [ No CAS ]

References: [1]Patent: US9598419,2017,B1 .

29
[ 50840-23-8 ]
4-(4-(((6-methoxy-2-(6-methylimidazo[1,2-a]pyrimidin-2-yl)benzofuran-4-yl)oxy)methyl)-5-methyl-thiazol-2-yl)morpholine [ No CAS ]

References: [1]Patent: US9598419,2017,B1 .

30
[ 50840-23-8 ]
[ 1446333-79-4 ]
7-fluoro-3-(6-methylimidazo[1,2-a]pyrimidin-2-yl)-2H-chromen-2-one hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	In ethanol; at 95℃; for 16h;	Step A: Following the procedure in Example 36, Part 3, 3-(2-bromoacetyl)-7-fluoro-2H-chromen-2-one (0.855 g, 3.0 mmol) and <strong>[50840-23-8]5-methylpyrimidin-2-amine</strong> (0.327 g, 3.0 mmol) in EtOH (6.0 mL) gave 7-fluoro-3-(6-methylimidazo[1,2-a]pyrimidin-2-yl)-2H-chromen-2-one hydrobromide (0.37 g, 42%) as a pale yellow solid. MS m/z 296.2 [M+H]+.

References: [1]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 371; 372.

31
[ 50840-23-8 ]
[ 1192810-68-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1261 - 1266.

32
[ 50840-23-8 ]
[ 102368-13-8 ]
C₆H₅N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 2h;	General procedure: Isoquinolin-3-amine (3.23 g, 22.4 mmol) was added to a solution of 1,1'-thiocarbonyldipyridin-2(1H)-one (5.20 g, 22.4 mmol) in dichloromethane (50 mL) at room temperature. The reaction was stirred for 2 h, then purified by flash chromatography on silica gel (0-10% ethyl acetate in hexanes). Product fractions were combined and concentrated in vacuo to give 3-isothiocyanatoisoquinoline(3.9 g, 93 %) as a white solid.

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1261 - 1266.

33
[ 50840-23-8 ]
(R)-2-chloro-4-((8-chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)benzoic acid [ No CAS ]
(R)-2-chloro-4-((8-chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)-N-(5-methylpyrimidin-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A 0.5 - 2.0 mL microwave vessel was charged with carboxylic acid VII (251 mg, 0.534 mmol) and this was dissolved in NMP (2 mL). HATU (223 mg, 0.587 mmol) andDIPEA (0.102 mL, 0.587 mmol) were then added and the resultant mixture was stirred at room temperature for 30 min. 2-amino-5-trifluoromethylpyridine (130 mg, 0.801 mmol) was then added and the vessel was tightly sealed with a crimp top. The resultant mixture was heated thermally in a heating block to 110 C for 16 h. The mixture was then diluted with EtOAc and washed with successively with sat. NH4Cl (aq) (1X), sat. NaHCO3 (aq) (1X), H2O (1X) and brine (1X). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was then purified by FCC (12 g SiO2, gradient elution with 0-5% MeOH/DCM). The semi-pure material obtained was then further purified by FCC (12 g SiO2, gradient elution with 0-100% EtOAc/hexanes) and then purified further by FCC (12 g SiO2, gradient elution with 0-5% MeOH/EtOAc) to provide 170 mg (52%) of 11d.

References: [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3601 - 3605.

34
[ 50840-23-8 ]
(R)-4-((8-chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)-2-methylbenzoic acid [ No CAS ]
(R)-4-((8-chloro-2,5-dioxo-3-(pyridin-2-ylmethyl)-2,3-dihydro-1H-benzo[e][1,4]diazepin-4(5H)-yl)methyl)-2-methyl-N-(5-methylpyrimidin-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A 0.5 - 2.0 mL microwave vessel was charged with carboxylic acid VII (251 mg, 0.534 mmol) and this was dissolved in NMP (2 mL). HATU (223 mg, 0.587 mmol) andDIPEA (0.102 mL, 0.587 mmol) were then added and the resultant mixture was stirred at room temperature for 30 min. 2-amino-5-trifluoromethylpyridine (130 mg, 0.801 mmol) was then added and the vessel was tightly sealed with a crimp top. The resultant mixture was heated thermally in a heating block to 110 C for 16 h. The mixture was then diluted with EtOAc and washed with successively with sat. NH4Cl (aq) (1X), sat. NaHCO3 (aq) (1X), H2O (1X) and brine (1X). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was then purified by FCC (12 g SiO2, gradient elution with 0-5% MeOH/DCM). The semi-pure material obtained was then further purified by FCC (12 g SiO2, gradient elution with 0-100% EtOAc/hexanes) and then purified further by FCC (12 g SiO2, gradient elution with 0-5% MeOH/EtOAc) to provide 170 mg (52%) of 11d.

References: [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3601 - 3605.

35
[ 50840-23-8 ]
tert-butyl 1-(5-(5-formyl-1H-pyrazol-1-yl)-1,3,4-thiadiazol-2-yl)piperidine-4-carboxylate [ No CAS ]
1-(5-(5-(((5-methylpyrimidin-2-yl)amino)methyl)-1H-pyrazol-1-yl)-1,3,4-thiadiazol-2 -yl)piperidine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylsilane; trifluoroacetic acid; In acetonitrile; at 80℃;Sealed tube;	A mixture of 5-4 (200 mg, 0.55 mmol), <strong>[50840-23-8]5-methylpyrimidin-2-amine</strong> (120 mg, 1.1 mmol), TFA (188 mg, 1.65 mmol), Et3SiH (191 mg, 1.65 mmol), MeCN (20 mL) and a stirring bar was sealed in a 100-mL screw-top tube and stirred at 80 C overnight. The reaction was treated with a saturated aqueous solution of NaHCO3 (20 mL) and evaporated in vacuum to remove most of MeCN. The residue was diluted with EtOAc (50 mL) and washed with brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 2/1 to 1/1) to give the title compound as a white solid (210 mg, 83%).

References: [1]European Journal of Medicinal Chemistry,2019,vol. 172,p. 1 - 15.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 50840-23-8 ]

Amines

A299723 [39268-71-8]

5-Ethylpyrimidin-2-amine

Similarity: 0.90

A142818 [109-12-6]

Pyrimidin-2-amine

Similarity: 0.86

A184199 [1193-74-4]

4,5-Dimethylpyrimidin-2-amine

Similarity: 0.83

A204264 [1753-48-6]

2-Aminopyrimidine-5-carbonitrile

Similarity: 0.83

A404991 [120747-85-5]

2-Aminopyrimidine-5-methanol

Similarity: 0.83

Related Parent Nucleus of
[ 50840-23-8 ]

Pyrimidines

A299723 [39268-71-8]

5-Ethylpyrimidin-2-amine

Similarity: 0.90

A142818 [109-12-6]

Pyrimidin-2-amine

Similarity: 0.86

A184199 [1193-74-4]

4,5-Dimethylpyrimidin-2-amine

Similarity: 0.83

A204264 [1753-48-6]

2-Aminopyrimidine-5-carbonitrile

Similarity: 0.83

A404991 [120747-85-5]

2-Aminopyrimidine-5-methanol

Similarity: 0.83

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CAS No.: 50840-23-8

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