[ CAS No. 89641-18-9 ]

Name: 89641-18-9|2,4-Dimethoxypyrimidine-5-boronic acid|97%
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Quality Control of [ 89641-18-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 89641-18-9 ]

CAS No. :	89641-18-9	MDL No. :
Formula :	-	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LKGKUACPLXCVOF-UHFFFAOYSA-N
M.W :	-	Pubchem ID :	2736209
Synonyms :

Calculated chemistry of [ 89641-18-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	44.84
TPSA :	84.7 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) :	-7.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.28
Log Po/w (WLOGP) :	-1.83
Log Po/w (MLOGP) :	-2.16
Log Po/w (SILICOS-IT) :	-1.65
Consensus Log Po/w :	-1.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.95
Solubility :	20.8 mg/ml ; 0.113 mol/l
Class :	Very soluble
Log S (Ali) :	-1.04
Solubility :	16.8 mg/ml ; 0.0913 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.8
Solubility :	29.2 mg/ml ; 0.159 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.47

Safety of [ 89641-18-9 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Application In Synthesis of [ 89641-18-9 ]

* 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 [ 89641-18-9 ]
Downstream synthetic route of [ 89641-18-9 ]

[ 89641-18-9 ] Synthesis Path-Upstream 1~3

1
[ 298-12-4 ]
[ 89641-18-9 ]
[ 52606-02-7 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8201 - 8205[2] Angew. Chem., 2017, vol. 129, # 28, p. 8313 - 8317,5

2
[ 56686-16-9 ]
[ 89641-18-9 ]

Reference： [1] Journal of Materials Chemistry C, 2017, vol. 5, # 37, p. 9638 - 9650

3
[ 7647-01-0 ]
[ 89641-18-9 ]

Reference： [1] Journal of Materials Chemistry C, 2017, vol. 5, # 37, p. 9638 - 9650

[ 89641-18-9 ] Synthesis Path-Downstream 1~69

1
[ 724466-73-3 ]
[ 89641-18-9 ]
[ 1025840-19-0 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 984 - 1000

2
[ 5315-25-3 ]
[ 89641-18-9 ]
[ 952402-48-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 4h;Heating / reflux;	Preparation 49: 2,4-Dimethoxy-5-(6-methyl-pyridin-2-yl)-pyrimidine (Prep49); 2,4-Di-methoxy-pyrimidine-5-boronic acid (500 mg, 2.72 mmol) was dissolved in degassed n-PrOH (40 ml_) and then 2-bromo-6-methylpyridine (660 mg, 3.8 mmol), <n="90"/>Na2CO3 (865 mg, 8.16 mmol), PPh3 (215 mg, 0.8 mmol) and Pd(OAc)2 (50 mg, 0.22 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated and the crude was partitioned between water and Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (2-8) to give 300 mg of the title compound (47% yield). MS (ES) (mlz): 232.3 [M+H]+.1H-NMR (DMSO-CJ6) delta: 8.83 (s, 1 H), 7.62 - 7.78 (m, 2 H), 7.21 (d, 1 H), 4.02 (s, 3 H), 3.97 (s, 3 H), 2.52 (s, 3 H).

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 87-88

3
[ 3430-13-5 ]
[ 89641-18-9 ]
[ 952402-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 1.5h;Heating / reflux;	Preparation 56: 2,4-Dimethoxy-5-(6-methyl-pyridin-3-yl)-pyrimidine (Prep56); 2,4-Dimethoxy-pyrimidine-5-boronic acid (commercially available from Aldrich, 830 mg, 4.5 mmol) was dissolved in degassed n-PrOH (10 ml.) and then 3-bromo-6- methylpyridine (600 mg, 3.5 mmol), Na2CO3 (956 mg, 9 mmol), PPh3 (90 mg, 0.35 mmol) and Pd(OAc)2 (78 mg, 0.35 mmol) were added. The suspension was stirred at reflux for 1.5 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by SCX cartridge washing with MeOH and then collecting the product with MeOH-NH4OH (95-5) to give 500 mg of the title compound (62% yield). MS (ES) {mlz): 232.3 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 91

4
[ 952402-57-2 ]
[ 89641-18-9 ]
[ 952402-58-3 ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 120h;	Preparation 58: 1-(3,3-Dimethoxy-propyl)-5-(6-methyl-pyridin-3-yl)-1 H-pyrimidine- 2,4-dione (Prep58); 5-(6-methyl-pyridin-3-yl)-1 H-pyrinnidine-2,4-dione hydrochloride (Prep57, 385 mg, 1.62 mmol), K2CO3 (224 mg, 1.62 mmol) and 3-bromo-1 ,1dimethoxy-propane (commercially available from Aldrich, 183 mg, 1.0 mmol) were suspended in dry DMF (8 ml_). After stirring the reaction at room temperature for 24 hours, additional 3-bromo-1 ,1dimethoxy- propane ( 180mg, 0.98mmol) was added portionwise over a period of 96h. Water was added and the mixture was washed with diethyl ether. The aqueous layer was then extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated to give 320 mg of the final compound that was used without further purification in the next step (48% yield). MS (ES) (mlz): 410.4 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 92

5
[ 952402-60-7 ]
[ 89641-18-9 ]
[ 952402-61-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 4h;Heating / reflux;	Preparation 61 : 5-(2,4-Dimethyl-oxazol-5-yl)-2,4-dimethoxy-pyrimidine (Prep61); 2,4-Dimethoxy-pyrimidine-5-boronic acid (840 mg, 4.6 mmol) was dissolved in degassed n-PrOH (40 mL) and then 5-iodo-2,4-dimethyl-oxazole (PrepthetaO, 850 mg, 3.8 mmol),Na2CO3 (848 mg, 8 mmol), PPh3 (332 mg, 1.3 mmol) and Pd(OAc)2 (85 mg, 0.38 mmol) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate.The organic phase was dried (Na2SO4) and evaporated. The crude was purified by SCX cartridge to give 600 mg of the title compound (66% yield).MS (ES) {mlz): 236.2 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 93

6
[ 144100-07-2 ]
[ 89641-18-9 ]
[ 952402-74-3 ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 3h;Heating / reflux;	Preparation 74: 5-(6-Fluoro-pyridin-2-yl)-2,4-dimethoxy-pyrimidine (Prep74); <n="102"/>2,4-Dimethoxy-pyrimidine-5-boronic acid (966 mg, 5.3 mmol) was dissolved in degassed n-PrOH (60 ml) and then 2-bromo-6-fluoropyridine (850 mg, 4.8 mmol), Na2CO3 (1.676 g, 15.8 mmol), PPh3 (400 mg, 1.52 mmol) and Pd(OAc)2 (116 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPrOH to give 650 mg of the title compound as a white powder (52% yield). MS (ES) (mlz): 236.2 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 99-100

7
[ 69045-79-0 ]
[ 89641-18-9 ]
[ 952402-91-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 2.5h;Heating / reflux;	Preparation 90: 5-(6-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep90); 2,4-Dimethoxy-pyrimidine-5-boronic acid (1.14 g, 6.26 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-chloro-5-iodopyridine (1 g, 4.2 mmol), Na2CO3 (884 mg, 15.8 mmol), PPh3 (109 mg, 0.42 mmol) and Pd(OAc)2 (46 mg) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated under vacuum and the <n="111"/>crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated to give the title compound that was used in the next step without further purification (quantitative yield). MS (ES) (mlz): 252.2 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 108-109

8
[ 17282-01-8 ]
[ 89641-18-9 ]
[ 952402-99-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 2h;Heating / reflux;	Preparation 98: 5-(2-Fluoro-5-methylpyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep98); 2,4-Dimethoxy-pyrimidine-5-boronic acid (842 mg, 4.60 mmol) was dissolved in degassed n-PrOH (55 ml) and then <strong>[17282-01-8]2-fluoro-3-bromo-5-methylpyridine</strong> (800 mg, 4.21 mmol), Na2CO3 (1.46 g, 13.77 mmol), PPh3 (348 mg, 1.33 mmol) and Pd(OAc)2 (101 mg, 0.45 mmol) were added. The suspension was stirred at reflux for 2 hours. After cooling, the solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The residue was triturated with Et2O to give 350 mg of the title compound as a gray powder (31 % yield). MS (ES) (mlz): 250.2 [IvRH]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 112

9
[ 55758-02-6 ]
[ 89641-18-9 ]
[ 952403-03-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	palladium diacetate; triphenylphosphine; In propan-1-ol; for 3h;Heating / reflux;	Preparation 102: 3-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile (Prep102); 2,4-Dimethoxy-pyrimidine-5-boronic acid (1 g, 5.46 mmol) was dissolved in degassed n- PrOH (30 ml) and then <strong>[55758-02-6]2-cyano-3-bromopyridine</strong> (950 mg, 5.19 mmol), Na2CO3 (1.65 g,15.56 mmol), PPh3 (393 mg, 1.5 mmol) and Pd(OAc)2 (114 mg, 0.51 mmol) were added.The suspension was stirred at reflux for 3 hours. After cooling, the solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate.The organic phase was washed with brine, dried (Na2SO4) and evaporated. The residue was triturated with iPrOH to give 1 g of the title compound as a white powder (76% yield).MS (ES) (mlz): 243.2 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 114

10
[ 3430-22-6 ]
[ 89641-18-9 ]
[ 952403-13-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 3h;Heating / reflux;	Preparation 110: 5-(4-Methyl-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep110); 2,4-Dimethoxypyrimidine-5-boronic acid (1.3 g, 7.23 mmol) was dissolved in degassed n- PrOH (20 ml) and then 4-methyl-3-bromo-pyridine (830 g, 4.82 mmol), Na2CO3 (1.02 g, 9.64 mmol), PPh3 (126 mg, 0.48 mmol) and Pd(OAc)2 (40 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated to give the title compound that was used without further purification in the next step (quantitative yield). MS (ES) (mlz): 232.2 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 118

11
[ 884494-48-8 ]
[ 89641-18-9 ]
[ 952403-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 2.5h;Heating / reflux;	Preparation 114: 5-(2-Fluoro-6-methyl-pyridin-3-yl)-2,4-dimethoxy-pyrimidine (Prep114); 2,4-Dimethoxy-pyrimidine-5-boronic acid (1.16 g, 6.32 mmol) was dissolved in degassed n-PrOH (22 ml) and then <strong>[884494-48-8]2-fluoro-6-methyl-3-iodopyridine</strong> (870 mg, 3.67 mmol), Na2CO3 (778 mg, 7.34 mmol), PPh3 (96 mg, 0.37 mmol) and Pd(OAc)2 (41 mg added in three portions) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPrOH to give 691 mg of the title compound (75% yield). MS (ES) (mlz): 250.1 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 120

12
[ 65202-53-1 ]
[ 89641-18-9 ]
[ 952403-21-3 ]

Yield	Reaction Conditions	Operation in experiment
34%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 5h;Heating / reflux;	Preparation 120: 3-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridazine (Prep120); 2,4-Dimethoxy-pyrimidine-5-boronic acid (2.05 g, 11.21 mmol) was dissolved in degassed n-PrOH (80 ml) and then 3-iodo-pyridazine (Prep119, 2.1 g, 10.19 mmol), Na2CO3 (3.24 g, 30.57 mmol), PPh3 (890 mg, 3.40 mmol) and Pd(OAc)2 (180 mg, 0.8 mmol) were added. The suspension was stirred at reflux for 5 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and evaporated. The residue was triturated with iPrOH to afford 750 mg of the title compound as a white powder (34% yield). MS (ES) (mlz): 219.2 [M+H]+.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 123

13
[ 32111-21-0 ]
[ 89641-18-9 ]
[ 952403-25-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; for 4h;Heating / reflux;	Preparation 124: 2,4-Dimethoxy-5-pyrazin-2-yl-pyrimidine (Prep124); 2,4-Dimethoxy-pyrimidine-5-boronic acid (1.33 g, 7.27 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-iodo-pyrazine (1.0 g, 4.85 mmol), Na2CO3 (1.02 g, 9.70 mmol), PPh3 (127 mg, 0.48 mmol) and Pd(OAc)2 (54 mg) were added. The suspension was stirred at reflux for 4 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH- NH4OH (99-1-0.1 ) to give 481 mg of the title compound (45% yield).MS (ES) (mlz): 219.1 [M+H]*.

Reference： [1]Patent: WO2007/113232,2007,A1 .Location in patent: Page/Page column 125

14
[ 870689-53-5 ]
[ 89641-18-9 ]
5-(2,4-dimethoxy-pyrimidin-5-yl)-1-(1-ethyl-propyl)-6-methyl-1H-imidazo[4,5-b]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium sulfate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 24h;Heating / reflux;	Step B: 5-(2,4-Dimethoxy-pyrim idin-5 -yl)- I -( I -ethyl-propyl)-6-methyl- H- imidazo[4,5-b]pyrazine: I -( I -Ethyl-propyl)-5,6-dimethyl- I H-imidazo[4,5-b]pyrazine is taken in 6ml toluene followed by the addition of Pd(PPh3)4 (100mg), boronic acid(282mg, 1.5 eq. ) and Na2SO4(1.0M in water, 2ml). The resulting mixture is heated for 24 hours. The reaction mixture is extracted with ethyl acetate and dried with anhydrous Na2S04. Purification by TLC gives product 170mg, yield: 50%.

Reference： [1]Patent: WO2005/115399,2005,A2 .Location in patent: Page/Page column 43

15
[ 862730-04-9 ]
[ 89641-18-9 ]
1-isopropyl-3-(2,4-dimethoxypyrimidin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 80℃;	Synthesis of 1-isopropyl-3-(2,4-dimethoxypyrimidin-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA66); A solution 2,4-dimethoxypyrimidin-5-yl-5-boronic acid (106 mg, 0.58 mmol) in EtOH (3.3 ml) was added to a solution of <strong>[862730-04-9]3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine</strong> (70 mg, 0.23 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80 C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by silica gel column chromatography [MeOH-CH2Cl2, 2:98] to yield BA66. ESI-MS (M+H)+ m/z calcd 316.1, found 316.0.

Reference： [1]Patent: US2007/293516,2007,A1 .Location in patent: Page/Page column 20

16
[ 1139879-57-4 ]
[ 89641-18-9 ]
N-(5-(2,4-dimethoxypyrimidin-5-yl)pyrimidin-4-yl)-L-4-(N,N-dimethylcarbamyloxy)phenylalanine tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In monoethylene glycol diethyl ether; for 6h;Heating / reflux;	Method S Suzuki Coupling Procedure III An ethyleneglycol dimethyl ether/2M Na2CO3 (1: 1 by volume) solution of tetrakis (triphenylphosphine)palladium (0.04 eq), N-(5-iodopyrimidin-4-yl)-L-4- (N,N-dimethylcarbamyloxy)phenylalanine tert-butyl ester (1.0 eq. ), the boronic acid (1.1 eq) and lithium chloride (3.0 eq ) was heated to reflux for approximately six hours. The cooled reaction mixture was diluted with ethyl acetate and washed with water, brine, dried (MgS04), filtered and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate/hexanes to afford the desired product.

Reference： [1]Patent: WO2005/97162,2005,A2 .Location in patent: Page/Page column 529; 553

17
[ 591-50-4 ]
[ 89641-18-9 ]
[ 685866-81-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 20 - 60℃; for 12h;Heating / reflux;	[00376] To 2,4-Dimethoxypyrimidine-5-boronic acid (200mg, 10.6mmol), IODOBENZENE (326mg, 1. 60MMOL) and K3P04 (900MG, 4.24mmol) in DMSO (5ML, purged with Ar) was added 1, 1'BIS (diphenylphosphino) ferrocene palladium chloride, complex with dichloromethane (12MG) and the reaction solution was heated to 60 C in a sealed tube. The solution was heated for 2h, stirred at room temperature for 10HR and filtered through celite. The solution was poured into sat. NAHC03 to give a gray solid. This material was collected, dissolved in ethyl acetate, dried (Na2SO4). Flash chromatography 0 to 2% methanol in dichloromethane gave 2, 4-DIMETHOXY-5-PHENYL-PYRIMIDINE (171mg, 75% yield). HPLC tr=5. 62min (83%), FIA m/e 217.2 (M+H), HNMR (500 MHz, CDC13) USDNo.8. 25 (1H, s), 7.45- 7.29 (5H, m), 4.00 (3H, s), 3.98 (3H, s).

Reference： [1]Patent: WO2004/37814,2004,A1 .Location in patent: Page 179-180

18
[ 868395-72-6 ]
[ 89641-18-9 ]
(R)-2,4-Dimethoxy-5-[4'-(1-pyrrolidin-1-ylethyl)-biphenyl-4-yl]-pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; at 150℃; for 5h;Microwave;	(R)-(+-)-1-[1-(4'-bromobiphenyl-4-yl)-ethyl]-pyrrolidine (165 mg, 0.5 mmol) and 2,4-dimethoxypyrimidine-5-boronic acid (138 mg, 0.75 mmol) in 3.8 mL ethanol containing 0.8 mL water were combined with sodium carbonate (212 mg) and tetrakis(triphenylphosphine)palladium(0) in a 5 mL microwave tube. The reactants were heated in a microwave apparatus for 300 min at 150 C., cooled to room temperature and the crude product was purified as described previously. The free base was isolated as a clear oil that was converted to the hydrochloride salt as a white solid, 73 mg. Mass spectrum (m/z) calcd for C24H27N3O2: 389.50; obsd: 391, 390 (M+1, 100%), 319, 279. 1H-nmr (CDCl3, 400 MHz)-delta 1.43 (d, 3H), 1.77 (bs, 4H), 2.42 (bs, 2H), 2.63 (bs, 2H), 3.22 (q, 1H), 4.03 (s, 6H), 7.24 (s, 1H), 7.40 (m, 2H), 7.55 (m, 3H), 7.62 (m, 2H), 8.30 (s, 1H).

Reference： [1]Patent: US2005/245543,2005,A1 .Location in patent: Page/Page column 19-20

19
[ 873663-35-5 ]
[ 89641-18-9 ]
[ 873663-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium fluoride;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In methanol; for 18h;Heating / reflux;	A mixture of 2-[3-(l-ter?-butoxycarbonylpiperidin-4-ylcarbonylamino)phenyl]-4,6-dichloropyrimidine (0.19 g), <strong>[89641-18-9]2,4-dimethoxypyrimidin-5-ylboronic acid</strong> (0.085 g), caesiumfluoride (0.064 g), a [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(IT) 1:1 complexwith methylene chloride (0.01 g) and methanol (20 ml) was stirred under an atmosphere ofnitrogen and heated to reflux for 18 hours. The resultant reaction mixture was evaporated andthe residue was partitioned between methylene chloride and a saturated aqueous sodiumbicarbonate solution. The organic solution was washed with brine, dried over magnesiumsulphate and evaporated. The residue was purified by column chromatography on silica usinga 1:1 mixture of hexane and ethyl acetate as eluent. There was thus obtained2-[3-(l-fer?-butoxycarbonylpiperidin-4-ylcarbonylamino)phenyl]-6-chloro-4-(2,4-dimethoxypyrimidin-5-yl)pyrimidine as a solid (0.067 g); NMR Spectrum: (CDCls)1.48 (s, 9H), 1.65-1.85 (m, 2H), 1.89-2.01 (m, 2H), 2.43 (t, 1H), 2.74-2.87 (m, 2H), 4.11 (s,3H), 4.19 (s, 3H), 7.27 (s, 1H), 7.46 (t, 1H), 7.55 (s, 1H), 7.9 (s, 1H), 8.07 (d, 1H), 8.24 (d,1H), 8.29-8.32 (m, 1H).

Reference： [1]Patent: WO2006/5915,2006,A1 .Location in patent: Page/Page column 86

20
N-(2(R)-methyl-2-tetrahydrofuroyl)-(L)-4-iodophenylalanine [ No CAS ]
[ 89641-18-9 ]
[ 327617-62-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; dichloromethane; ethyl acetate;	EXAMPLE 184 N-(2(R)-Methyl-2-tetrahydrofuroyl)-(L)-4-(2,4-dimethoxy-5-pyrimidinyl)-phenylalanine Coupling of 200 mg (0.479 mmol) of N-(2(R)-methyl-2-tetrahydrofuroyl)-(L)-4-iodophenylalanine, methyl ester (from Example 111, Step B) with 106 mg (0.575 mmol) of 2,4-dimethoxypyrimidine-5-boronic acid mediated by Pd(PPh3)4 was carried out as described in Reference Example 2, Step B. The reaction was acidified with a few drops of saturated HCl in ethyl acetate. The solvents were removed in vacuo and the residue was purified by preparative TLC on silica gel eluted with 1% AcOH in 5% CH3OH/CH2Cl2 to give 167.8 mg of the desired product. MS m/e=416.22 (M+H+) 500 MHz 1H NMR (CD3OD): delta 1.24 (s, 3H); 1.70-1.90 (m, 3H), 2.22 (m, 1H), 3.11 (m, 1H); 3.27 (m, 1H); 3.88 (m, 2H); 4.01 (m, 6H); 4.68 (brs, 1H); 7.25 (d, 2J=8.00); 7.41 (d, 2H, J=8.00); 8.11 (bd, 1H); 8.22 (brs, 1H).

Reference： [1]Patent: US6420418,2002,B1

21
trifluoromethanesulfonic acid 2-({(3,5-bis-trifluoromethyl-benzyl)-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amino}-methyl)-4-trifluoromethyl-phenyl ester [ No CAS ]
[ 89641-18-9 ]
(3,5-bis-trifluoromethyl-benzyl)-[2-(2,4-dimethoxy-pyrimidin-5-yl)-5-trifluoromethyl-benzyl]-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;palladium diacetate; 1,1'-bis(di-tert-butylphosphino)ferrocene; In 1,4-dioxane; at 80℃; for 4h;	Trifluoromethanesulfonic acid 2-({(3,5-bis-trifluoromethyl-benzyl)-[5- (2 -methanesulfonyl-ethoxy) -pyrimidin-2 -yl] -amino}-methyl) -4- trifluoromethyl-phenyl ester (l lOmg) is dissolved in 1,4-dioxane (2ml) and thereto are added 2,4-dimethoxy-pyrimidine-5-boronic acid (70mg), palladium acetate (13.2mg), l, l'-bis(di-tert-butylphosphino)ferrocene (28mg) and tripotassium phosphate (62mg) and the mixture is stirred under nitrogen atmosphere at 80C for 4 hours. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and water, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane : ethyl acetate = 2: 1) to give (3,5-bis- trifluoromethyl-benzyl) - [2 - (2 , 4-dimethoxy-pyrimidin-5-yl) -5- trifluoromethyl-benzyl]-[5-(2-methanesulfonyl-ethoxy)-pyrimidin-2-yl]- amine (34mg). MS (m/z): 740 [M+H]+.

Reference： [1]Patent: WO2007/88996,2007,A1 .Location in patent: Page/Page column 182; 184

22
[ 622860-38-2 ]
[ 55552-70-0 ]
[ 1765-93-1 ]
[ 10365-98-7 ]
[ 32316-92-0 ]
[ 5122-94-1 ]
[ 98546-51-1 ]
[ 78887-39-5 ]
[ 128796-39-4 ]
[ 1692-25-7 ]
[ 135145-90-3 ]
[ 94839-07-3 ]
[ 1423-26-3 ]
[ 150255-96-2 ]
[ 126747-14-6 ]
[ 179113-90-7 ]
[ 139301-27-2 ]
[ 87199-15-3 ]
[ 89641-18-9 ]
[ 308103-40-4 ]
[ 149104-88-1 ]
[ 622860-55-3 ]
9-hydroxy-4-(4-methylsulfanylphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
[ 622860-48-4 ]
4-(4-fluorophenyl)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
4-(9-hydroxy-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazol-4-yl)-benzonitrile [ No CAS ]
3-(9-Hydroxy-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazol-4-yl)-benzonitrile [ No CAS ]
4-(2,5-dichlorophenyl)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
9-Hydroxy-4-(3-hydroxymethyl-phenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
4-(2-Acetyl-phenyl)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
9-hydroxy-4-(4-methanesulfonylphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
9-hydroxy-4-(4-trifluoromethylphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
9-hydroxy-4-(3-trifluoromethylphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
4-Furan-2-yl-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
9-Hydroxy-4-(3-trifluoromethoxy-phenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
9-Hydroxy-4-(4-trifluoromethoxy-phenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
9-hydroxy-4-naphthalen-2-yl-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
4-(1,3-benzodioxol-5-yl)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
4-(2,4-dimethoxy-pyrimidin-5-yl)-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
4-biphenyl-4-yl-9-hydroxy-6H-pyrrolo[3,4-c]carbazole-1,3-dione [ No CAS ]
N-[3-(9-hydroxy-1,3-dioxo-1,2,3,6-tetrahydro-pyrrolo[3,4-c]carbazol-4-yl)-phenyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 90℃; for 4h;Combinatorial reaction / High throughput screening (HTS);Product distribution / selectivity;	EXAMPLE 36The Preparation of a series of compounds using multiple parallel synthetic techquires from 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione prepared as in Example 7 Combichem Procedure 1; In a 8 ml screw cap vial was added a solution of 9-Hydroxy-4-iodo-6H-pyrrolo[3,4-c]carbazole-1,3-dione, (0.1 mmol) prepared as in example 7 in dioxane (1 ml), a solution of Reagent 1 (see table) (0.1 mmol) in 1:1 dioxane/2.5 M K2CO3 (1 ml) and [1,1'Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (0.003 g, 0.0037 mmol). The vial was capped and the reaction mixture was shaken for 4 hours at 90 C. After cooling to room temperature, the solution was was removed under vacuum. Purification was carried out via reverse-phase HPLC (3% n-propanol in acetonitrile and 3% n-propanol in water as the eluent; C-18 column). The products were characterised by mass spectral analysis (See Table 1).

Reference： [1]Patent: US7094798,2006,B1 .Location in patent: Page/Page column 40-42

23
[ 606978-01-2 ]
[ 89641-18-9 ]
[ 1029806-26-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;palladium diacetate; triphenylphosphine; In isopropyl alcohol;	l-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4- dihydro-lH-isoquinoline-2-carboxylic acid tert-butyl ester 25 was synthesized by the Suzuki coupling of l-(4-bromobenzyl)-6,7-dimethoxy-3,4-dihydro-lH-isoquinoline- 2-carboxylic acid tert-butyl ester 1 with 2,4-dimethoxypyrimidine-5-boronicacid 24 using Palladium(II) acetate, triphenylphosphine, and Na2CO3 . Reaction of compound 25 with 2 M HCl solution in diethylether yielded l-[4-(2,4-dimethoxypyrimidin-5- yl)benzyl]-6,7-dimethoxy-l,2,3,4-tetrahydroisoquinoline hydrochloride salt 26 (Scheme-7).

Reference： [1]Patent: WO2008/64329,2008,A1 .Location in patent: Page/Page column 14; 16; 29

24
[ 107346-32-7 ]
[ 89641-18-9 ]
4-amino-8-(2,4-dimethoxy-pyrimidin-5-yl)-N-propyl-cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%		EXAMPLE 5 4-amino-8-(2,4-dimethoxypyrimidin-5-yl)-N-propyl-cinnoline-3-carboxamide Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (100 mg, 0.324 mmol) and <strong>[89641-18-9](2,4-dimethoxypyrimidin-5-yl)boronic acid</strong> (125 mg, 0.68 mmol) were reacted to afford the title compound (33 mg, 28% yield) as a white solid. 1H NMR (300 MHz, CDCl3) delta 8.52 (bm, 1H), 8.33 (s, 1H), 7.91 (dd, J=7.7, 2.0 Hz, 1H), 7.70-7.77 (m, 2H), 4.06 (s, 3H), 3.93 (s, 3H), 3.46 (apparent q, J=6.5 Hz, 2H), 1.67(apparent sextet, J=7.2 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H). MS APCI, m/z=369 (M+H) HPLC 1.69 min.
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 90℃;	General procedure: 4-Amino-7-X-8-(aryl)-N-(alkyl)-cinnoline-3-carboxamide (X = H or F).The corresponding bromide-precursor(III) (1 equiv), the corresponding aryl boronic acid reagent (2.2 equiv), tetrakis(triphenylphosphine)palladium(0) (0.05 equiv) and potassium carbonate (3.0 equiv) in DME/ethanol/water (7/2/3) were heated at 90 C, monitored by LC/MS. The reaction concentration was 0.3 M. Upon completion, the reaction mixture was cooled to room temperature, diluted with chloroform and washed with water. The chloroform layer was dried with magnesium sulfate, and evaporated to constant mass. The crude product was loaded onto a silica gel column, and eluted with 0-10% methanol in methylene chloride to give a yellow or tan solid. The solid was further crystalized from ether/methylene chloride, or purified by HPLC to give a white, yellow or tan solid as the desired product in 50-85% yield.

Reference： [1]Patent: US2008/318925,2008,A1
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2927 - 2938

25
4-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide [ No CAS ]
[ 89641-18-9 ]
4-amino-N-cyclopropyl-8-(2,4-dimethoxypyrimidin-5-yl)cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		EXAMPLE 96 4-amino-N-cyclopropyl-8-(2,4-dimethoxypyrimidin-5-yl)cinnoline-3-carboxamide Using Method A, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (143 mg, 0.47 mmol) and 2,4-dimethoxypyrimidine-5-boronic acid (171 mg, 0.94 mmol) were reacted. After purification the title compound (133 mg, 78% yield) was obtained as a white solid. 1H NMR (300 MHz, CDCl3) delta 8.51 (bm, 1H), 8.31 (s, 1H), 7.89 (a dd, J=2.3, 7.4 Hz, 1H), 7.75 (m, 2H), 4.06 (s, 3H), 3.92 (s, 3H), 2.96 (m, 1H), 0.88 (m, 2H), 0.65 (m, 2H). MS APCI, m/z=367, HPLC 2.07 min

Reference： [1]Patent: US2008/318925,2008,A1

26
[ 942438-80-4 ]
[ 89641-18-9 ]
4-amino-N-cyclopropyl-8-(2,4-dimethoxypyrimidin-5-yl)-7-fluoro-cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		EXAMPLE 163 4-amino-N-cyclopropyl-7-fluoro-8-(2,4-dimethoxypyrimidin-5-yl)cinnoline-3-carboxamide Using Method A, 4-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide (178 mg, 0.48 mmol) and 2,4-dimethoxypyrimidin-5-boronic acid (176 mg, 0.96 mmol) were reacted. After purification the title compound (73 mg, 39% yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) delta 9.04 (d, J=4.9 Hz, 1H), 8.57 (dd, J=5.6, 9.3 Hz, 1H), 8.37 (s, 1H) 7.77 (t, J=9.1 Hz, 1H), 3.99 (s, 3H), 3.84 (s, 3H), 2.93 (m, 1H), 0.70(m, 4H). MS APCI, m/z=385.

Reference： [1]Patent: US2008/318925,2008,A1

27
[ 942438-94-0 ]
[ 89641-18-9 ]
4-amino-N-cyclobutyl-8-(2,4-dimethoxypyrimidin-5-yl)-7-fluoro-cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 130 4-amino-N-cyclobutyl-8-(2,4-dimethoxypyrimidin-5-yl)-7-fluoro-cinnoline-3-carboxamide Using Method A, 4-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide (175 mg) and 2,4-dimethoxypyrimidin-5-yl boronic acid (207 mg) were reacted to afford the title compound (88 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) delta 9.24 (d, 1H), 8.57 (m, 1H), 8.38 (s, 1H), 7.77 (m, 1H), 4.49 (m, 1H), 4.00 (s, 3H), 3.84 (s, 3H), 2.26-2.10 (m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=399 (M+H).

Reference： [1]Patent: US2008/318925,2008,A1

28
[ 93704-68-8 ]
[ 89641-18-9 ]
[ 1126422-30-7 ]

Yield	Reaction Conditions	Operation in experiment
39%	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; for 6h;Heating / reflux;	Step 2: 1B 1 C; To a mixture of 3-bromo-5-chloro-lH-indole-2-carboxylic acid ethyl ester, IB (1.00 g, 3.31 mmol), 2,4-dimethoxypyrimidine-5-boronic acid (0.73 g, 3.97 mmol), [1,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(H) with dichloromethane complex (1 :1) (0.26 g, 0.32 mmol) in DME (15 mL) was added a solution of sodium carbonate (4.5 mL of 1.5 <n="97"/>M, 6.75 mmol) via a syringe. The reaction mixture was stirred at reflux for 6 h before cooled down to room temperature. The mixture was diluted with dichloromethane (50 mL), and was filtered through a pad of celite. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (20 % ethyl acetate in hexanes) to provide the product 1C as a white solid (0.47 g, 39% yield). M.S. found for Ci7Hj6ClN3O4: 362.2 (M+H)+.
39%	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; for 6h;Heating / reflux;	Step 2:; To a mixture of 3-bromo-5-chloro-lH-indole-2-carboxylic acid ethyl ester, 4B (1.00 g, 3.31 mmol), 2,4-dimethoxypyrimidine-5-boronic acid (0.73 g, 3.97 mmol), [1,1 '- bis(diphenylphosphino)ferrocene]dichloropalladium(?) with dichloromethane complex (1 :1) (0.26 g, 0.32 mmol) in DME (15 mL) was added a solution of sodium carbonate (4.5 mL of 1.5 M, 6.75 mmol) via a syringe. The reaction mixture was allowed to stir at reflux for 6 h before cooled down to room temperature. The mixture was diluted with dichloromethane (50 mL), and was filtered through a pad of celite. The filtrate was concentrated in vacuo. The resulting residue was purified using flash chromatography on silica gel (20 % ethyl acetate in hexanes) <n="148"/>to provide the product 4C as a white solid (0.47 g, 39% yield). M.S. found for C17Hi6ClN3O4: 362.2 (M+H)+.

Reference： [1]Patent: WO2009/32123,2009,A2 .Location in patent: Page/Page column 95-96
[2]Patent: WO2009/32124,2009,A1 .Location in patent: Page/Page column 146-147

29
[ 3034-53-5 ]
[ 89641-18-9 ]
[ 1138450-56-2 ]

Yield	Reaction Conditions	Operation in experiment
		2-bromo-1 ,3-thiazole (commercially available from Aldrich, 0.165 ml, 1.829 mmol) was dissolved in degassed 1 ,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (106 mg, 0.091 mmol) was added. The reaction mixture was stirred at room temperature for 15min. [2,4- bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich, 707 mg, 3.84 mmol) and 5ml_ of degassed 1 M aqueous solution of NaHCO3 were added to the reaction mixture under N2 atmosphere. After 2h30min stirring at 900C, the reaction mixture was diluted with water and extracted with DCM. The collected organic phases were evaporated. The residue was purified by flash chromatography eluting with cyclohexane/EtOAc 5:1. 294 mg of the title compound were isolated as a yellow solid. MS (ES) (mlz): 224.06 [M+H]+.

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 54-55

30
[ 89641-18-9 ]
[ 7064-38-2 ]
[ 1138450-83-5 ]

Yield	Reaction Conditions	Operation in experiment
41.6%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 4h;	2,4-dimethoxypyrimidine-5-boronic acid (commercially available from Aldrich, 0.264 g, 1.435 mmol), 4-iodo-5-methylisoxazole (0.200 g, 0.957 mmol) and TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) (0.221 g, 0.191 mmol) in 1 ,2- Dimethoxyethane (DME) (5 ml) were stirred until dissolution of reactants, then sodium carbonate 1 M (2.87 ml, 2.87 mmol) was added and the mixture heated at 9O0C for 4h. Solids were filtered off by filtration tube and washed by DCM , organic phase was washed by a saturated solution of ammonium chloride (20 mL), brine (20 mL), dried upon sodium sulphate and evaporated.Residue was purified on silica (biotage 25M, Cy/AcOEt 8:2) obtaining N4735-2-1 : 5-(5- methyl-4-isoxazolyl)-2,4-bis(methyloxy)pyrimidine (0.088 g, 0.398 mmol, 41.6 % yield). MS (ES) (mlz): 223 [M+H]+.

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 70

31
[ 89641-18-9 ]
[ 298694-30-1 ]
[ 1138450-46-0 ]

Yield	Reaction Conditions	Operation in experiment
		4-bromo-2-methyl-1 ,3-thiazole (commercially available from Frontier, 300mg, 1.685 mmol) was dissolved in 1 ,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (97 mg, 0.084 mmol) was added and the reaction mixture was stirred at room temperature for 15 min. [2,4- bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich , 651 mg, 3.54 mmol) and 1 M/H2O sol. of NaHCO3 (4.60 ml, 4.60 mmol) were added thereto. The reaction mixture was heated at 900C for 2.5 h and left at room temperature overnight. The mixture was then diluted with dichloromethane (20 ml) and washed with water (20 ml). The organic layer was separated through an hydrophobic frit and concentrated. The obtained crude was purified by flash chromatography eluting with Cyclohexane/AcOEt 8/2. 290 mg of the title compound were isolated as a white solid. MS (ES) (mlz): 238.1 [M+H]+, 260.1 [M+Na]+

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 51

32
[ 54044-79-0 ]
[ 89641-18-9 ]
[ 1138450-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Microwave irradiation;Product distribution / selectivity;	In a microwave vial, 2-bromo-5-methyl-1 ,3,4-thiadiazole (0.6 g, 3.26 mmol), [2,4- bis(methyloxy)-5-pyrimidinyl]boronic acid (0.780 g, 4.36 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.754 g, 0.652 mmol) in 1 ,2-Dimethoxyethane (DME) (12 ml) were stirred until dissolution of reactants, then sodium carbonate 1 M (9.78 ml, 9.78 mmol) was added and the mixture microwaved for 10 min at 15O0C. In another microwave vial, 2-bromo-5-methyl-1 ,3,4-thiadiazole (commercially available from Akos, 0.522 g, 2.84 mmol), [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (0.780 g, 4.36 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.656 g, 0.568 mmol) in 1 ,2- Dimethoxyethane (DME) (12 ml) were stirred until dissolution of reactants, then sodium carbonate 1 M (8.51 ml, 8.51 mmol) was added and the mixture microwaved for 10 min at 15O0C. The two reaction mixtures were combined, water and AcOEt (50 +50 ml.) were added and organic layer separated. Combined organic layers were washed by water (3 x 50 ml_), dried upon sodium sulphate and concentrated under reduced pressure. Residue was purified by flash chromatography (Cy: EtOAc 1 :1 ) to give the title compound (637 mg, 2.272 mmol). 1H NMR (CHLOROFORM-d) delta ppm 9.30 (s, 1 H) 4.18 (s, 3 H) 4.1 1 (s, 3 H) 2.84 (s, 3 H)

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 47

33
[ 34203-25-3 ]
[ 89641-18-9 ]
[ 1138450-73-3 ]

Yield	Reaction Conditions	Operation in experiment
78%		2-iodo-4-methyl-1 ,3-thiazole (prepared according to procedure described in JACS 123 (6), 1017-1022, (2001 ), 250 mg, 1.1 11 mmol) was dissolved in 1 ,2-Dimethoxyethane (DME) (4.629 ml). Pd(Ph3P)4 (64.2 mg, 0.056 mmol) was added and the mixture was stirred at room temperature for 10 minutes. 1 M aqueous sol. Sodium bicarbonate (4.443 ml, 4.44 mmol) and <strong>[89641-18-9][2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid</strong> (409 mg, 2.222 mmol) were added and the resulting mixture was stirred at 85C for 2 hours. The mixture was allowed to cool to rt and it was diluted with DCM (5 ml_). The aqueous was separated and extracted with DCM (2X5ml_). The organics were combined and dried (Na2SO4 then rotaevaporator) to give a yellow solid that was purified by silica chromatography (Biotage SP1 , 25+M), eluting with DCM:MeOH from 100:0 to 9:1 to afford the title compound as a pale yellow solid (280 mg, 78% yield). MS (ES) (m/z): 238 [M+H]+

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 64-65

34
[ 28599-52-2 ]
[ 89641-18-9 ]
C₁₁H₁₃N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 4-bromo-2,5-dimethyl-1 ,3-thiazole (commercially available from Apollo Scientific Ltd, 410 mg, 2.135 mmol) in 1 ,2-Dimethoxyethane (DME) (6.5 mL), Tetrakis(triphenylphosphine)palladium (123 mg, 0.107 mmol) was added and the mixture was stirred at rt for 30 minutes. Then <strong>[89641-18-9][2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid</strong> ( <n="62"/>commercially available from Aldrich, 916 mg, 4.48 mmol) and 1 M Sodium bicarbonate aqueous solution (5.83 ml_, 5.83 mmol) were added. The reaction mixture was then stirred at 9O0C for 2.5h and left stirring at rt overnight. The day after the mixture was diluted with DCM and washed with water. Organic layer was dried and concentrated under vacuum . Crude product was first purified by flash chromatography (eluent: Cy/AcOEt 65:35) and further purified by SCX cartridge affording 5-(2,5-dimethyl-1 ,3- thiazol-4-yl)-2,4-bis(methyloxy)pyrimidine with minor unknown impurities that was used in the next step without further purification.

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 60-61

35
[ 29947-25-9 ]
[ 89641-18-9 ]
[ 1138450-41-5 ]

Yield	Reaction Conditions	Operation in experiment
		2-iodo-4,5-dimethyl-1 ,3-thiazole (prepared in a similar manner to that described in JACS 123 (6), 1017-1022, (2001 ), 250 mg, 1.046 mmol) was dissolved in 1 ,2-Dimethoxyethane(DME) (4.357 ml). Tetrakis(triphenylphosphine)palladium(0) (60.4 mg, 0.052 mmol) was added and the mixture was stirred at room temperature for 10 minutes. Sodium bicarbonate (4.183 ml, 4.18 mmol) and <strong>[89641-18-9][2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid</strong>(385 mg, 2.091 mmol) were added and the resulting mixture was stirred at 85C for 2 hours. The mixture was allowed to cool to rt and left standing at rt over the week end.The mixture was diluted with DCM (5 ml_), the aqueous phases was separated and extracted with DCM (2X5ml_). The organics were combined and dried over sodium sulphate to give a yellow solid that was purified by silica chromatography, eluting with DCM:MeOH from 100:0 to 95:5 to afford the title compound as a pale yellow solid (143 mg). <n="50"/>MS (ES) (m/z): 252 [M+H]+.

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 48-49

36
[ 24340-77-0 ]
[ 89641-18-9 ]
[ 1138450-50-6 ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[24340-77-0]4-bromoisothiazole</strong> (commercially available from Aurora, 500 mg, 3.05 mmol) was dissolved in degassed 1 ,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (176 mg, 0.152 mmol) was added thereto. The reaction mixture was stirred at room temperature for 15min. [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich ,1178 mg, 6.40 mmol) and 5ml_ of degassed 1 M/H2O solution of NaHCO3 were added to the reaction mixture under N2 atm. After 2h30min stirring at 900C the mixture was diluted with water and extracted with DCM. The collected organic phases were evaporated. The residue was purified by flash chromatography eluting with cyclohexane/EtOAc 5:1. 686 mg of the title compound were isolated as a yellow solid. MS (ES) {mlz): 224.06 [M+H]+.

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 53

37
[ 930-42-7 ]
[ 89641-18-9 ]
[ 1138450-79-9 ]

Yield	Reaction Conditions	Operation in experiment
4.7%		4-bromo-3-methylisothiazole (prepared according to literature: Isothiazoles. II. Isothiazolealdehydes and isothiazolyl ketones. Buttimore, D.; Jones, D. H.; Slack, R.; Wooldridge, K.R.H. Journal of the Chemical Society, 1963, 2032-9), (160 mg, 0.899 mmol) was dissolved in 1 ,2-Dimethoxyethane (DME) (3744 mul). Pd(Ph3P)4 (51.9 mg, 0.045 mmol) was added and the mixture was stirred at room temperature for 10 minutes. 1 M aqueous sol. A saturated solution of Sodium bicarbonate (3.6ml_ 3.59 mmol) and[2,4- bis(methyloxy)-5-pyrimidinyl]boronic acid (331 mg, 1.797 mmol) were added and the resulting mixture was stirred at 85C for 2 hours and at rt overnight. The mixture was diluted with NaHCO3 sat sol and DCM (2 ml. each), the aqueous was separated and extracted with DCM (2X5ml_). The organics were combined and dried (rotaevaporator) to give a brown solid that was purified by silica chromatography (Biotage SP1 , 12+M), eluting with Cyclohexane: EtOAc from 100:0 to 7:3 to afford the title compound as a brown solid (10 mg, 4.7% yield). <n="70"/>A second batch of compound was prepared following the above described procedure starting from 46mg of 4-bromo-3-methylisothiazole amd obtaining 21.6mg of the title compound.MS (ES) (m/z): 238 [M+H]+.1H NMR (400 MHz, CHLOROFORM-d) d ppm 2.43 (s, 3 H) 4.03 (s, 3 H) 4.07 (s, 3 H)8.19 (s, 1 H) 8.52 (s, 1 H)

Reference： [1]Patent: WO2009/43883,2009,A1 .Location in patent: Page/Page column 68-69

38
[ 89641-18-9 ]
potassium (2,4-dimethoxypyrimidin-5-yl)trifluoroborate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 973 - 980

39
potassium (2,4-dimethoxypyrimidin-5-yl)trifluoroborate [ No CAS ]
[ 89641-18-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With iron(III) chloride; water; In tetrahydrofuran; at 20℃; for 1h;	General procedure: Potassium phenyltrifluoroborate (184 mg, 1.00 mmol) was added to a solution of iron trichloride (185 mg, 1.10 mmol) in 3 mL of 1:1 THF/water. The mixture was stirred at room temperature for 30 min. The reaction mixture was then passed through a short column containing neutral absorption alumina. The alumina was then washed with a mixture of ethyl acetate/hexanes (2:1) to obtain phenylboronic acid (105 mg, 86%). [The boronic acid products can also be isolated by simple extraction techniques.] All products possessed physical and spectral characteristics (13C, 1H, 11B NMR) in accord with literature values.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 6534 - 6536
[2]Journal of Organic Chemistry,2009,vol. 74,p. 7364 - 7369

40
SnCl_2.2H₂O [ No CAS ]
[ 1206775-33-8 ]
[ 96042-30-7 ]
[ 89641-18-9 ]
[ 74-88-4 ]
[ 1232361-56-6 ]

Yield	Reaction Conditions	Operation in experiment
12 mg (34%)	With hydrogen bromide; sodium methylate; sodium carbonate;Pd(PPh3)4; In methanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; mineral oil;	step 4-To a solution of 200c (116 mg, 0.276 mmol) in DMF (5 mL) was added sodium hydride (0.022, 0.550 mmol, 60% mineral oil dispersion). After 20 min, methyl iodide (0.040 mL, 0.643 mmol) was added and the resulting suspension was stirred overnight. The reaction mixture was diluted with EtOAc, thrice washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluding with an EtOAc/hexane gradient (5% to 15% EtOAc) to afford 81 mg (68%) of 200d as an orange oil. Reduction of the nitro group (step 5) was carried out with SnCl2.2H2O in DMF/EtOAc in accord with the procedure described in step 2 of Example 1 to afford 202a. Sulfonylation of the amine to afford 202b (step 6) is carried out in accord with the procedure described in step 3 of example 1 step 7-A tube was charged with 202b (100 mg, 0.207 mmol), 2,4-dimethoxy-pyrimidin-5-yl boronic acid (207 mg, 0.261 mmol), Pd(PPh3)4 (27 mg, 0.023 mmol), Na2CO3 (61 mg, 0.576 mmol), MeOH (3 mL) and DCM (1 mL), sealed and irradiated in a microwave synthesizer at 115 C. for 30 min. The reaction mixture was concentrated, diluted with EtOAc, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluding with an EtOAc/hexane gradient (50 to 100% EtOAc) to afford 35 mg (31%) of 204 as a cream colored solid. step 8-A solution of 204 (35 mg, 0.065 mmol), 48% HBr (0.05 mL, 0.436 mmol) in HOAc (3 mL) was heated at 60 C. overnight in a sealed tube. The reaction mixture was carefully poured into a mixture of sat'd. aq. NaHCO3/ice which was extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered and dried in vacuo to afford 206 which was used in the final step without addition purification. step 9-A solution of 206 (0.065 mmol), sodium methoxide (10 mL, 5 mmol, 0.5M in methanol) and methanol (10 mL) was stirred at RT overnight. The reaction mixture was concentrated, diluted with EtOAc and acidified with 6N HCl. The combined EtOAc extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified on a preparatory SiO2 plate developed with 2:1 EtOAc/hexane to afford 12 mg (34%) of I-39 as an off-white solid.

Reference： [1]Patent: US2010/158860,2010,A1

41
2,3-diazabicyclo[2.2.1]hept-5-ene-N,N'-di-tert-butyl dicarboxylate [ No CAS ]
[ 89641-18-9 ]
[ 1026988-74-8 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3160 - 3163

42
C₂₃H₁₈ClF₃N₄O [ No CAS ]
[ 89641-18-9 ]
[ 1222998-41-5 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 7146 - 7155

43
[ 1308247-17-7 ]
[ 89641-18-9 ]
[ 1308247-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; water; toluene; at 115℃; for 0.333333h;sealed tube; Inert atmosphere; microwave irradiation;	step 2-; A 2-5 mL microwave tube was charged with 118 (85 mg, 181 mumol), 115 (39.8 mg, 217 mumol), Na2CO3 (57.6 mg, 543 mumol), MeOH (0.4 mul), toluene (0.2 muL) and H2O (0.2 muL). The mixture was bubbled with argon for 10 min then Pd(PPh3)4 (10.5 mg, 9.05 mumol) was added. Argon was bubbled through the solution another 5 min. The vial was sealed and irradiated in a microwave reactor at 115 C. for 20 min. The mixture was cooled, diluted with EtOAc and water and aqueous layer was neutralized with 1N HCl. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (25-50% EtOAc) to afford 56.6 mg of 120.

Reference： [1]Patent: US2010/311760,2010,A1 .Location in patent: Page/Page column 48

44
[ 1257665-64-7 ]
[ 89641-18-9 ]
[ 1257665-79-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 8654 - 8657

45
[ 1041114-10-6 ]
[ 89641-18-9 ]
[ 1262388-20-4 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 534 - 547

46
[ 1304777-36-3 ]
[ 89641-18-9 ]
[ 1304777-40-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2484 - 2488

47
C₂₉H₄₅BrN₆O₆ [ No CAS ]
[ 89641-18-9 ]
C₃₅H₅₂N₈O₈ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 3041 - 3049

48
[ 30384-96-4 ]
[ 89641-18-9 ]
[ 1304017-58-0 ]

Yield	Reaction Conditions	Operation in experiment
47.43%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; for 3h;Reflux;	Intermediate 8: 6-(2, 4-dimethoxypyrimidin-5-yl) imidazo [1, 2-a] pyridine-3- carbaldehyde 1402-1596-bromoimidazo [1, 2-a] pyridine-3-carbaldehyde (Compound of step 1 of Intermediate 1, 200 mg, 0.89 mmol), 2,4-dimethoxypyrimidin-5-ylboronic acid (212.57 mg, 1.15 mmol), dichlorobis (triphenylphosphine) palladium (II) (20 mg, 10% mmol) and 2M aqueous Na2C03 (1 mL) were added to DMF (8 mL) and refluxed for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with H20 and brine. The solvent was evaporated to obtain crude product, which was purified by column chromatography (silica gel, 1% methanol in chloroform) to obtain the title compound. Yield: 47.43 %; lU NMR (DMSO-d6; 300 MHz): delta 9.97 (s, 1H), 9.59 (s, 1H), 8.56-8.58 (d, 2H, J=4.5Hz), 7.88-7.98 (m, 2H), 3.96 (s, 3H), 3.98(s, 3H); MS: m/z 285.1(M+1) +

Reference： [1]Patent: WO2011/55320,2011,A1 .Location in patent: Page/Page column 47

49
[ 622834-91-7 ]
[ 89641-18-9 ]
[ 355835-48-2 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4187 - 4206

50
[ 109-09-1 ]
[ 89641-18-9 ]
[ 1334531-02-0 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5180 - 5183

51
[ 52334-81-3 ]
[ 89641-18-9 ]
[ 1334531-16-6 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5180 - 5183

52
[ 870-50-8 ]
[ 89641-18-9 ]
1-(2,4-dimethoxy-pyrimidin-5-yl)-1,2-hydrazinedicarboxylic acid 1,2-bis(1,1-dimethylethyl) ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(II) acetate monohydrate; In methanol; at 65℃; for 1h;	General procedure: 6-Methoxypyridin-3-ylboronic acid (115 mg, 0.75 mmol), di-tert-butylazodicarboxylate ?DBAD? (115 mg, 0.5 mmol) and Cu(II)OAc-H2O (5.1 mg, 0.025 mmol) were combined in 3 mL MeOH in a 20 mL scintillation vial and heated for 1 h at 65 C. The mixture was cooled to room temperature and 2-phenylacetaldehyde (90 mg, 0.75 mmol) was added followed by addition of 2 mL 4 N HCl in dioxane and the mixture was placed in an 80 C heating block for 18 h. The reaction was cooled to room temperature and volatiles were removed in vacuo to give a crude oil which was partitioned between 25 mL of satd aq NaHCO3 and 100 mL CH2Cl2. Organics were extracted, dried (MgSO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography though silica gel using ethyl acetate in heptanes to elute providing 78 mg (70%) of 5-methoxy-3-phenyl-1H-pyrrolo[3,2-b]pyridine (Table 1, entry 1a) as a yellow solid.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 564 - 569

53
[ 89641-18-9 ]
[ 1353942-39-8 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 564 - 569

54
[ 89641-18-9 ]
[ 1374116-20-7 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 4402 - 4413

55
[ 1390665-75-4 ]
[ 89641-18-9 ]
[ 1390666-33-7 ]

Yield	Reaction Conditions	Operation in experiment
10%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In N,N-dimethyl-formamide; at 60℃; for 8h;Inert atmosphere;	General procedure: Under a nitrogen atmosphere, to a mixture of compound 13 (1 g, 2 mmol, 1 eq), 3,4 - methylenedioxyphenyl boronic acid (0.4 g , 2.46 mmol, 1.2 eq) in DMF (5 mL) was added palladium (0) tetrakis(triphenylphosphine) (0.162 g, 0.14 mmol 0.07 eq). The mixture was stirred at 60 oC for 8 h, diluted with EtOAc, and quenched with saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by normal phase column (EtOAc in hexane 25%-50%) to yield the desired product (0.92 g, 1.7mmol, 86% yield).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4536 - 4539

56
[ 120157-97-3 ]
[ 89641-18-9 ]
[ 1417540-94-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; at 90℃; for 18h;Inert atmosphere;	Example 2 Synthesis of tert-butyl 4-(2,4-dimethoxypyrimidin-5-yl)phenethylcarbamate Industrial methylated spirits (IMS; 15 mL) and water (5 mL) were degassed thoroughly. tert-butyl 4-bromophenethylcarbamate (1.08 g, 3.63 mmol), sodium carbonate (1.54 g, 14.52 mmol), palladium tetrakis (0.42 g, 0.36 mmol) and 2,4-dimethoxy-5-pyrimidinylboronic acid (1.00 g, 5.44 mmol) were added and the reaction mixture heated to 90 C. for 18 hours. No starting material was observed by LCMS. Water (100 ml) and ethyl acetate (300 ml) were added and the organic layer separated. The organic layer was washed with water (100 ml), dried (MgSO4) and concentrated to give a yellow oil. The crude residue was subject to column chromatography (20 to 60% ethyl acetate/hexane) to give a yellow oil, tert-butyl 4-(2,4-dimethoxypyrimidin-5-yl)phenethylcarbamate, which crystallized on standing (1.18 g, 3.28 mmol, 91%).

Reference： [1]Patent: US2013/5755,2013,A1 .Location in patent: Page/Page column 17

57
[ 25245-35-6 ]
[ 89641-18-9 ]
5-(2,5-dimethoxyphenyl)-2,4-dimethoxypyrimidine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7944 - 7960

58
[ 16932-44-8 ]
[ 89641-18-9 ]
5-(2,6-dimethoxyphenyl)-2,4-dimethoxy-pyrimidine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7944 - 7960

59
[ 16932-44-8 ]
[ 89641-18-9 ]
5-(2,6-dimethoxyphenyl)-4-iodo-2,6-dimethoxypyrimidine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7944 - 7960

60
[ 1193-72-2 ]
[ 89641-18-9 ]
5-(2,4-dichlorophenyl)-2,4-dimethoxypyrimidine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7944 - 7960

61
[ 29110-74-5 ]
[ 89641-18-9 ]
[ 1450994-02-1 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 12877 - 12885

62
[ 81167-60-4 ]
[ 89641-18-9 ]
2-(2,4-dimethoxypyrimidin-5-yl)-4-t-butylpyridine [ No CAS ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 14613 - 14624

63
[ 4519-46-4 ]
[ 89641-18-9 ]
C₁₀H₁₂N₂O₄ [ No CAS ]

Reference： [1]MedChemComm,2016,vol. 7,p. 1340 - 1351

64
[ 298-12-4 ]
[ 89641-18-9 ]
[ 52606-02-7 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 8201 - 8205
Angew. Chem.,2017,vol. 129,p. 8313 - 8317,5

65
[ 56686-16-9 ]
[ 89641-18-9 ]

Reference： [1]Journal of Materials Chemistry C,2017,vol. 5,p. 9638 - 9650

66
[ 25676-75-9 ]
[ 89641-18-9 ]
[ 1138450-59-5 ]

Reference： [1]Organometallics,2018,vol. 37,p. 4224 - 4241

67
[ 56423-63-3 ]
[ 89641-18-9 ]
[ 952403-25-7 ]

Reference： [1]Organometallics,2018,vol. 37,p. 4224 - 4241

68
[ 1458-01-1 ]
[ 89641-18-9 ]
3,5-diamino-N-carbamimidoyl-6-(2,4-dimethoxypyrimidin-5-yl)pyrazine-2-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

69
[ 1458-01-1 ]
[ 89641-18-9 ]
methyl 3,5-diamino-6-(2,4-dimethoxypyrimidin-5-yl)pyrazine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; toluene;Inert atmosphere; Reflux;	General procedure: <strong>[1458-01-1]Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate</strong> 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
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
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
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. 89641-18-9 ]

Quality Control of [ 89641-18-9 ]

Related Doc. of [ 89641-18-9 ]

Product Details of [ 89641-18-9 ]

Calculated chemistry of [ 89641-18-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 89641-18-9 ]

Application In Synthesis of [ 89641-18-9 ]

[ 89641-18-9 ] Synthesis Path-Upstream 1~3

[ 89641-18-9 ] Synthesis Path-Downstream 1~69

Related Functional Groups of [ 89641-18-9 ]

Organoboron

Ethers

Related Parent Nucleus of [ 89641-18-9 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 89641-18-9 ]

Related Parent Nucleus of
[ 89641-18-9 ]