[ CAS No. 1439-10-7 ] {[proInfo.proName]}

Name: 1439-10-7|4-Amino-5-bromopyrimidine|98%
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Quality Control of [ 1439-10-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1439-10-7 ]

Product Details of [ 1439-10-7 ]

CAS No. :	1439-10-7	MDL No. :	MFCD00233962
Formula :	C₄H₄BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IIFAONYUCDAVGA-UHFFFAOYSA-N
M.W :	174.00	Pubchem ID :	10261576
Synonyms :

Calculated chemistry of [ 1439-10-7 ]

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 :	1.0
Molar Refractivity :	34.14
TPSA :	51.8 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.25
Log Po/w (XLOGP3) :	0.55
Log Po/w (WLOGP) :	0.83
Log Po/w (MLOGP) :	0.15
Log Po/w (SILICOS-IT) :	1.02
Consensus Log Po/w :	0.76

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.82
Solubility :	2.63 mg/ml ; 0.0151 mol/l
Class :	Very soluble
Log S (Ali) :	-1.21
Solubility :	10.7 mg/ml ; 0.0617 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.14
Solubility :	1.25 mg/ml ; 0.00721 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 1439-10-7 ]

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 [ 1439-10-7 ]

* 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 [ 1439-10-7 ]
Downstream synthetic route of [ 1439-10-7 ]

[ 1439-10-7 ] Synthesis Path-Upstream 1~3

1
[ 163133-86-6 ]
[ 1439-10-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With bromine; calcium carbonate In water at 60℃; for 0.75 h;	A variation of a published procedure7 was followed: 4- Aminopyrimidine (1.00 g, 10.5 mmol, 1.0 equiv) and CaCO3 (263 mg, 2.63 mmol, 0.25 equiv) were combined in H2O (20 mL) and Br2 (1.06 mL, 20.5 mmol, 2.0 equiv) was added dropwise. The reaction mixture was stirred at 60 °C for 45 minutes, cooled to room temperature, and then poured into CH2Cl2 (20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 × 20 mL). The combined organic layers were set aside. The aqueous layer was treated with 20percent aqueous K2CO3 until pH 9-10 was achieved, and the product precipitated. The precipitate was removed via filtration and dried, affording the product (1.08 g, 6.22 mmol, 59percent) as a light tan solid.

Reference： [1] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069
[2] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 81 - 86
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 12, p. 3654 - 3661
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 21, p. 5247 - 5250
[5] European Journal of Medicinal Chemistry, 2008, vol. 43, # 6, p. 1248 - 1260
[6] Yakugaku Zasshi, 1942, vol. 62, p. 315,333; dtsch. Ref. S. 95, 106[7] Chem.Abstr., 1951, p. 5150

2
[ 4595-59-9 ]
[ 163133-86-6 ]
[ 1439-10-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1285 - 1287

3
[ 56181-39-6 ]
[ 1439-10-7 ]

Reference： [1] Journal of the Chemical Society, 1955, p. 3478,3481

[ 1439-10-7 ] Synthesis Path-Downstream 1~28

1
[ 163133-86-6 ]
[ 1439-10-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With bromine; calcium carbonate; In water; at 60℃; for 0.75h;	A variation of a published procedure7 was followed: 4- Aminopyrimidine (1.00 g, 10.5 mmol, 1.0 equiv) and CaCO3 (263 mg, 2.63 mmol, 0.25 equiv) were combined in H2O (20 mL) and Br2 (1.06 mL, 20.5 mmol, 2.0 equiv) was added dropwise. The reaction mixture was stirred at 60 C for 45 minutes, cooled to room temperature, and then poured into CH2Cl2 (20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 × 20 mL). The combined organic layers were set aside. The aqueous layer was treated with 20% aqueous K2CO3 until pH 9-10 was achieved, and the product precipitated. The precipitate was removed via filtration and dried, affording the product (1.08 g, 6.22 mmol, 59%) as a light tan solid.

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 1064 - 1069
[2]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 81 - 86
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3654 - 3661
[4]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5247 - 5250
[5]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1248 - 1260
[6]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1942,vol. 62,p. 315,333; dtsch. Ref. S. 95, 106
Chem.Abstr.,1951,p. 5150

2
[ 56181-39-6 ]
[ 1439-10-7 ]

Reference： [1]Journal of the Chemical Society,1955,p. 3478,3481

3
[ 4595-59-9 ]
[ 163133-86-6 ]
[ 1439-10-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1285 - 1287

4
[ 1439-10-7 ]
[ 108-24-7 ]
[ 148214-51-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 81 - 86

7
[ 1439-10-7 ]
CuCN [ No CAS ]
[ 16357-69-0 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1943,vol. 63,p. 25,27
Chem.Abstr.,1951,p. 609

8
[ 1439-10-7 ]
[ 6312-73-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5247 - 5250
[2]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1248 - 1260

9
[ 1439-10-7 ]
[ 103-63-9 ]
5-phenethyl-pyrimidin-4-ylamine [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 341 - 344

10
[ 1439-10-7 ]
[ 688756-07-2 ]
[ 688755-94-4 ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 80℃; for 2h;	A mixture of the above boronate (0.204 g, 0.295 mmol), <strong>[1439-10-7]5-bromo-2-amino-pyrimidine</strong> (0.078 g, 0.443 mmol), and K2CO3 (0.122 g, 0.885 mmol) in 8 mL OF DIMETHOXYETHANE and 1.2 mL of water was flushed with N2 for 20 min. PDCL2 (DPPF) (0.025 g, 0.030 mmol) was added, and the reaction mixture was heated at 80 C for 2 h. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water and brine, and concentrated. The residue was purified by silica gel chromatography and preparative TLC to afford 0.062 g (32%) of the title compound (660.4, M+1)

Reference： [1]Patent: WO2004/41827,2004,A2 .Location in patent: Page 14-16

11
[ 1439-10-7 ]
[ 691906-94-2 ]
(S)-1-[(R)-5-[4-(4-amino-pyrimidin-5-yl)-benzyl]-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid (2-hydroxy-2-methyl-propyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 80℃; for 2h;	The above boronate (0.2 g) was dissolved in DME: H20 (5 mL: 1 mL). 2-Amino-3-bromo- pyrimidine (0.070 g) and potassium carbonate (0.092 g) were added and the flask was flushed with N2. The mixture was stirred for 20 min, and then PDCL2 (DPPF) CH2CL2 (0.020 g) was added. The mixture was heated at 80 C for 2h, cooled to room temperature and diluted with EtOAc. The mixture was filtered, concentrated and the residue was purified by silica gel chromatography to afford the title compound (0.080 g) as a foam (713.3, M+1)

Reference： [1]Patent: WO2004/41273,2004,A1 .Location in patent: Page/Page column 74075

12
[ 1439-10-7 ]
[ 915385-27-2 ]
(R)-5-[4-(4-Amino-pyrimidin-5-yl)-benzyl]-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 80℃; for 15.3333h;	A suspension of pinacol boronate (29) (506 mg), <strong>[1439-10-7]4-amino-5-bromopyrimidine</strong> (189 mg) and Na2CO3 (123 mg) in a dioxane (5.2 mL) water (2.6 mL) mixture is degasses with N2 for 20 minutes. PdCl2(dppf).CH2Cl2 (59 mg) is added and the reaction mixture is flushed with N2 The reaction is heated to 80 C. for 15 hr, then cooled to rt, diluted with water (10 mL) and brine (10 mL) and extracted with EtOAc. The combined organic layers are dried with MgSO4, filtered and concentrated. The material obtained is purified via reverse phase HPLC. The solvent is removed via lyophilization to give 120 mg of the title compound (1) as a white solid. (MS 544.95 M+1)

Reference： [1]Patent: US2006/264472,2006,A1 .Location in patent: Page/Page column 16-17

13
[ 1439-10-7 ]
[ 915385-28-3 ]
(R)-5-[4-(4-Amino-pyrimidin-5-yl)-benzyl]-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 80℃; for 18.3333h;	Pinacol boronate (31) (204 mg), <strong>[1439-10-7]4-amino-5-bromopyrimidine</strong> (92 mg) and Na2CO3 (52 mg) are suspended in a dioxane (2.2 mL) and water (1.1 mL) in a vial. N2 is bubbled through the mixture for 20 minutes. The Pd catalyst (2.9 mg) is added and the vial is flushed with N2, capped and sealed with parafilm. The reaction is heated to 80 C. for 18 hr. The reaction is cooled to rt, diluted with water (8 mL) and extracted with EtOAc. The combined organic layers are dried with MgSO4 and concentrated. The residue is purified via chromatography to afford 49.0 mg of the title compound. This material is further purified by reverse phase HPLC. The solvent is removed by lyophilization to give 44.3 mg of the trifluoroacetic acid salt of the desired amino pyrimidine (2) as a white powder. (MS 544.23 M+1)

Reference： [1]Patent: US2006/264472,2006,A1 .Location in patent: Page/Page column 17-18

14
[ 1439-10-7 ]
[ 24424-99-5 ]
[ 106-95-6 ]
[ 1049001-83-3 ]

Yield	Reaction Conditions	Operation in experiment
		Alternate Steps 1-2 4-Amino-5-bromopyrimidine is sequentially treated with (BOC)2O and 4-dimethylaminopyridine and then reacted with allyl bromide and an appropriate base to afford compound 12B.

Reference： [1]Patent: US2010/197562,2010,A1 .Location in patent: Page/Page column 39

15
[ 1439-10-7 ]
tert-butyl 6-bromoindoline-1-carboxylate [ No CAS ]
[ 1049001-59-3 ]

Yield	Reaction Conditions	Operation in experiment
		Steps 1-3 A mixture of N-Boc-6-bromoindoline (0.66 g, 2.2 mmol), bis(pinacolato)diboron (1.118 g, 4.4 mmol), KOAc (0.65 g, 6.6 mmol.), and PdCl2(dppf) (0.069 g, 0.08 mmol) in dioxane (8 mL) was heated at 100 C. for 1.5 h in a 15 mL sealed tube and then cooled to RT. The reaction was treated with <strong>[1439-10-7]4-amino-5-bromopyrimidine</strong> (0.76 g, 4.4 mmol) and aqueous K2CO3 (4 mL, 1M) and heated at 100 C. overnight. The mixture was diluted with aqueous K2CO3 and extracted with DCM. The organic extracts were dried over MgSO4 and concentrated. Chromatography (0-10% of (9:1 MeOH/NH3) in CH2Cl2) afforded 3A (657 mg) as a brown oil.

Reference： [1]Patent: US2010/197562,2010,A1 .Location in patent: Page/Page column 33

16
[ 1439-10-7 ]
[ 98-86-2 ]
[ 139962-80-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5316 - 5319

17
[ 1439-10-7 ]
[ 1356054-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; bis(pinacol)diborane;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 105℃; for 18h;Inert atmosphere; Sealed vial;	To a vial was added <strong>[1439-10-7]5-bromopyrimidin-4-amine</strong> (0.200 g, 1.149 mmol), bis(pinacolato)diboron (0.438 g, 1.724 mmol), and potassium acetate (0.338 g, 3.45 mmol). The vial was capped with a rubber septum and then evacuated and backfilled with N2. Dioxane (0.120 ml) was added via syringe through the septum. The reaction mixture was sparged with N2, then PdCi2(dppf)-CH2Ci2 (0.042 g, 0.057 mmol) was added. The septum was then replaced with a Teflon screw valve and the vial was sealed. The reaction mixture was heated at 105C in a metal pie block. After 18 h, reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with EtOAc. The filtrate was concentrated to afford a brown solid. MS (ESI) : m/z = 140.0 [M+H]+ HPLC Peak ret. T = 0.24 minutes was product (HPLC conditions: Column:Luna CI 8 4.6x30mm 3u A: 10:90 H20:ACN NH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow).

Reference： [1]Patent: WO2012/9510,2012,A1 .Location in patent: Page/Page column 67; 68

18
[ 1439-10-7 ]
[ 1356055-08-7 ]
[ 1356054-59-5 ]

Yield	Reaction Conditions	Operation in experiment
49.5%		To a suspension of potassium acetate (0.060 g, 0.614 mmol) in DMSO (1 mL) in a 2 dram vial was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (0.062 g, 0.246 mmol) followed by Example 104A (0.050 g, 0.123 mmol). This mixture was then sparged with 2 gas for 15 minutes. PdC12(dppf) (8.99 mg, 0.012 mmol) was then added followed by degassing for 5 additional minutes. The vial was sealed and then heated at 85C for 3 hours. The reaction mixture was cooled to room temperature and then Na2C03 (0.065 g, 0.614 mmol) was added followed by DME (1.0 mL), EtOH (0.5 mL) and water (0.5 mL). Next, <strong>[1439-10-7]5-bromopyrimidin-4-amine</strong> (0.028 g, 0.160 mmol) was then added followed by degassing with 2 for 10 minutes. Then,tetrakis(triphenylphosphine) palladium(O) (0.014 g, 0.012 mmol) was added followed by degassing for 5 additional minutes. The vial was then sealed and the mixture heated at 100C for 3 hours, cooled to room temperature and diluted with MeOH (5 mL). Filtration of this mixture and concentration gave the crude product as a brown solid. The crude material was purified by flash chromatography on silica using an ISCO system (12 g column, 40 mL/min, 0 - 7% MeOH in EtOAc over 20 minutes, rt = 1 1 minutes) to give Example 104 (23 mg, 0.061 mmol, 49.5 % yield) as an off-white solid. LC/MS(condition C): ret time = 1.39 min, MS (ES): m/z = 375.1 [M+H]+. ¾ NMR (500 MHz, DMSO-d6) delta ppm 6.98 (bs, 2 H); 7.41 (d, J=4.6 Hz, 1 H); 7.75 (dd, J=5.0, 8.8 Hz, 1 H); 7.84 (dt, J=2.9, 9.0 Hz, 1 H); 8.00 (dd, J=2.9, 9 Hz, 1 H); 8.31 (s, 1 H); 8.37 (s, 1 H); 8.53 (s, 1 H); 8.61 (d, J=4.6 Hz, 1 H).

Reference： [1]Patent: WO2012/9510,2012,A1 .Location in patent: Page/Page column 103; 104

19
[ 1439-10-7 ]
[ 73652-14-9 ]
[ 1097256-61-5 ]

Reference： [1]Synlett,2012,p. 443 - 447

20
[ 1439-10-7 ]
[ 73183-34-3 ]
[ 1356054-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 105℃; for 18h;Inert atmosphere;	Preparation 46A: 4-Aminopyrimidin-5-ylboronic acid[00148] To a vial was added <strong>[1439-10-7]5-bromopyrimidin-4-amine</strong> (0.200 g, 1.149 mmol), bis(pinacolato)diboron (0.438 g, 1.724 mmol), and potassium acetate (0.338 g, 3.45 mmol). The vial was capped with a rubber septum and then evacuated and backfilled with N2. Dioxane (volume: 0.120 ml) was added via syringe through the septum. The reaction mixture was sparged with N2, then l, l'-bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane complex (0.042 g, 0.057 mmol) was added. The septum was then replaced with a Teflon screw valve and the vial sealed. The reaction mixture was heated at 105 C in a metal pie block. After 18 h, the reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with EtOAc. The filtrate was concentrated to afford a brown solid. The crude material was used without further purification. MS (ESI) : m/z = 140.0 [M+H]+. HPLC Peak tr = 0.24 minutes. HPLC conditions: Column:Luna CI 8 4.6x30mm 3u A: 10:90 H20:ACN NH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow.

Reference： [1]Patent: WO2012/44537,2012,A1 .Location in patent: Page/Page column 58-59

21
[ 1439-10-7 ]
[ 163105-89-3 ]
[ 1253570-48-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5188 - 5219

22
[ 1439-10-7 ]
[ 94839-07-3 ]
[ 24966-28-7 ]

Yield	Reaction Conditions	Operation in experiment
44%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 110℃; for 0.5h;Microwave irradiation;	5-Bromopyrimidin-4-amine, SI-23 (400 mg, 2.30 mmol, 1.0 equiv) was dissolved in dioxane (7 mL) in a 20-mL microwave vial and to it was added 3,4-(methylenedioxy)phenylboronic acid (763 mg, 4.60 mmol, 2.0 equiv), aqueous Na2CO3 (2.0 M, 3.45 mL, 6.90 mmol, 3.0 equiv), and Pd(PPh3)4 (266 mg, 0.23 mmol, 0.10 equiv). The sealed vial was placed in a microwave reactor and heated at 110 C for 30 minutes. The crude reaction mixture was partitioned between CH2Cl2 (20 mL)/H2O (20 mL) and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2 × 20 mL), and the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude reaction mixture was purified via silica gel column chromatography using MeOH/CH2Cl2 (1:19) as the mobile phase, affording the product (220 mg, 1.02 mmol, 44%) as a light tan solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3654 - 3661

23
[ 1439-10-7 ]
[ 24424-99-5 ]
C₁₄H₂₀BrN₃O₄ [ No CAS ]

Reference： [1]Organic Process Research and Development,2015,vol. 19,p. 639 - 645

24
[ 1439-10-7 ]
[ 100-46-9 ]
C₁₁H₁₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
200 mg	With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2?,4?, 6?-triisopropyl- 1,1?-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane; In tetrahydrofuran; at 40℃;Inert atmosphere;	General procedure: Step 1: A vial equipped with a magnetic stir bar was charged with the ortho-haloaminopyridine and BrettPhos G1 precatalyst (6 mol %). The vial was sealed with a teflon screw cap, and evacuated and backfilled with argon three times. The amine (1 to 1.5 mol eq) was added via syringe, followed by LiHMDS solution (1M in THF, 2.5 mol eq). Amines that were solid at room temperature were added with the catalyst. The reaction mixture was stirred at 40 C for 4-18 h, until LC/MS indicated complete conversion of the starting material. The mixture was cooled to room temperature, diluted with dichloromethane, and poured into water. The organic phase was separated and the aqueous phase was extracted twice more with dichloromethane. The combined organic phases were dried over Na2SO4. The solvent was removed under reduced pressure.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2708 - 2712

25
[ 1439-10-7 ]
[ 97674-02-7 ]
C₆H₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 10℃; for 16h;	To a solution of 179 (260 mg, 1.5 mrnoi) in DMF (4 niL) is added tributyi(i ethoxyvinyl)tin (543 111g. 1,5 mrnoi) and Pd(dppf)C12 (110 mg, 0.15 mmol). After stirring at 100 C for 16 hours, the mixture is cooled to room temperature, filtered, concentrated, and purified by silica gel column chromatography (MeOH:DCM == 1:50) to give 180 as a brown solid (30 rng, 15% yield). (MS: [M±H I 3& 1)

Reference： [1]Patent: WO2017/176812,2017,A1 .Location in patent: Paragraph 0447

26
[ 1439-10-7 ]
[ 591-50-4 ]
[ 5059-31-4 ]

Yield	Reaction Conditions	Operation in experiment
37.9%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 110℃; for 24h;Inert atmosphere;	A mixture of <strong>[1439-10-7]5-bromopyrimidin-4-amine</strong> (1 g, 5.78 mmol), iodobenzene (1.18 g, 5.78 mmol), xantphos (334 mg, 0.578 mmol), sodium tert-butoxide (1.66 g, 17.34 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.52 g, 0.58 mmol) in dioxane was degassed with nitrogen, heated to 110 C. and stirred for 24 hours. The reaction was cooled to r.t, poured into water and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash chromatography (EtOAc/DCM=80%) to give 9H-pyrimido[4,5-b]indole (370 mg, 37.9% yield) as a yellow solid. LC/MS (ESI, m/z): [M+1]+=170.0.

Reference： [1]Patent: US2020/10468,2020,A1 .Location in patent: Paragraph 0762; 0763

27
[ 1439-10-7 ]
[ 73183-34-3 ]
C₁₀H₁₆BN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 12h;	Place <strong>[1439-10-7]4-amino-5-bromopyrimidine</strong> (15g, 1eq) in a dry two-necked bottle,Pinacol diborate (26.25g, 1.2eq), Pd (ddpf) 2Cl2 (3.15g, 0.05eq),Potassium acetate (25.2g, 3eq), then add 500mL of dioxane as a solution,Stir the reaction at 100 C for 12 hours, cool to room temperature, spin dry after the reaction is complete,Use dichloromethane and water solution, dry with magnesium sulfate and spin dry, then purify through silica gel column.A solid intermediate (8-a) was obtained with a yield of 70%.

Reference： [1]Patent: CN110981895,2020,A .Location in patent: Paragraph 0314-0317

28
[ 1439-10-7 ]
[ 2032-35-1 ]
[ 1049001-84-4 ]

Yield	Reaction Conditions	Operation in experiment
7.1%	With potassium hydrogensulfate In acetonitrile at 100℃; for 16h;	Step-1. Synthesis of 8-bromoimidazo[1,2-c]pyrimidine (Intermediate BB88) To a solution of Intermediate BB88-1 (0.350 g, 2 mmol) in acetonitrile (5 mL) were added KHSO4 (685 mg, 5.02 mmol, 2.5 eq) and bromo acetaldehyde diethyl acetal (0.4 g, 5.02 mmol, 2.5 eq). After stirring at 100° C. for 16 h, the reaction mixture was poured into water and extracted using 10% MeOH/DCM. The organic layer was washed with brine solution, dried over sodium sulfate, and concentrated under reduced pressure (0.3.5 g). The residue was purified by silica get chromatography eluting with 2.5% MeOH in DCM to afford Intermediate-BB88 (0.180 g, 7.1%). MS (ES): m/z 199.5 (M+H)+.

Reference： [1]Current Patent Assignee: NIMBUS SATURN; NIMBUS THERAPEUTICS INC; CHARLES RIVER LABORATORIES INTERNATIONAL INC - US2021/78996, 2021, A1 Location in patent: Paragraph 1257; 1258

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Code	Phrase
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1439-10-7 ] {[proInfo.proName]}

Quality Control of [ 1439-10-7 ]

Related Doc. of [ 1439-10-7 ]

Product Details of [ 1439-10-7 ]

Calculated chemistry of [ 1439-10-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1439-10-7 ]

Application In Synthesis of [ 1439-10-7 ]

[ 1439-10-7 ] Synthesis Path-Upstream 1~3

[ 1439-10-7 ] Synthesis Path-Downstream 1~28

Related Functional Groups of [ 1439-10-7 ]

Bromides

Amines

Related Parent Nucleus of [ 1439-10-7 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 1439-10-7 ]

Related Parent Nucleus of
[ 1439-10-7 ]