[ CAS No. 1375301-91-9 ] {[proInfo.proName]}

Name: 1375301-91-9|2-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine|97%
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SKU: A195044
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Quality Control of [ 1375301-91-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1375301-91-9 ]

Product Details of [ 1375301-91-9 ]

CAS No. :	1375301-91-9	MDL No. :	MFCD12032616
Formula :	C₁₃H₁₉BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DVGWUOHIWJBHKY-UHFFFAOYSA-N
M.W :	246.11	Pubchem ID :	45787283
Synonyms :

Calculated chemistry of [ 1375301-91-9 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.69
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	70.97
TPSA :	44.24 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.77
Log Po/w (WLOGP) :	1.59
Log Po/w (MLOGP) :	0.69
Log Po/w (SILICOS-IT) :	1.74
Consensus Log Po/w :	1.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.6
Solubility :	0.624 mg/ml ; 0.00254 mol/l
Class :	Soluble
Log S (Ali) :	-2.32
Solubility :	1.19 mg/ml ; 0.00482 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.86
Solubility :	0.0342 mg/ml ; 0.000139 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.08

Safety of [ 1375301-91-9 ]

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

Application In Synthesis of [ 1375301-91-9 ]

* 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 [ 1375301-91-9 ]
Downstream synthetic route of [ 1375301-91-9 ]

[ 1375301-91-9 ] Synthesis Path-Upstream 1~1

1
[ 304902-96-3 ]
[ 73183-34-3 ]
[ 1375301-91-9 ]

Yield	Reaction Conditions	Operation in experiment
39%	at 90℃; for 16 h;	A mixture of 12A(0.8 g, 4.02 mmol), Pd(dppf)C12 (147 mg, 0.20 mmol), KOAc (592 mg, 6.03 mmol) and bis(pinacolato)diboron (1.16 g, 4.82 mmol) in dioxane (20 mL) was heated to 90° C. overnight. After cooling, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (1/50 to 1/10 ethyl acetate/pet. ether) to give 12B (0.38 g, 39percent yield) as a yellow solid: ESI mlz 247.1 [M+H].

Reference： [1] Patent: US2018/291002, 2018, A1, . Location in patent: Paragraph 0427; 0429

[ 1375301-91-9 ] Synthesis Path-Downstream 1~5

1
[ 1044278-43-4 ]
[ 1375301-91-9 ]
C₁₈H₁₃ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	After degassing with N2, a mixture of 7-(bromomethyl)-4-chloroquinoline-2-carbonitrile (2-4, 650 mg, 2.31 mmol), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine (580 mg, 2.36 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (94 mg, 0.11 mmol), and K3P04 (1960 mg, 9.24 mmol) in 1,4- dioxane (13.7 mL) and H20 (1.7 mL) was heated at 100C for 30 min under microwave condition. The mixture was cooled to room temperature, and 1 -methyl-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)- lH-pyrazole (528 mg, 2.54 mmol) was added. After degassing with N2, the mixture was then heated at 115C for 30 min under microwave condition. The reaction mixture was cooled, diluted with H20 (10 mL) and the mixture was extracted with ethyl acetate (2x 50 mL). The combined organic fractions were washed with brine, dried (Na2S04), filtered and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with EtOAc/Hexane (0- 100%) to afford 7-((2-cyclopropylpyrimidin-5-yl)methyl)-4-(l -methyl- lH-pyrazol-4-yl)quinoline-2- carbonitrile (6-1, 649 mg, 77%). LRMS m/z (M+H)+ 367.3 found, 367.2 required.

Reference： [1]Patent: WO2013/66736,2013,A1 .Location in patent: Page/Page column 134

2
[ 1254567-35-5 ]
[ 1375301-91-9 ]
(3-amino-2,6-difluorophenyl)(5-(2-cyclopropylpyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100.0℃;	A mixture of (3-amino-2,6-difluorophenyl)(5-iodo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone (93 g, 233 mmol), <strong>[1375301-91-9]2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine</strong> (229 g, 466 mmol, 50% purity), potassium carbonate (97 g, 700 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (19.0 g, 23.3 mmol) in dioxane (930 mL) and water (465 mL) was heated at 100 C. for several hours. Upon cooling, the reaction mixture was diluted with water and extracted with a mixture of tetrahydrofuran and ethyl acetate. The organic layer was separated and concentrated under reduced pressure to give the crude product which was triturated with dichloromethane/methyl tert-butyl ether and filtered, washing with methyl tert-butyl ether to give the title compound as a tan solid (71 g, 78% yield).

Reference： [1]Patent: US2016/339025,2016,A1 .Location in patent: Paragraph 0229

3
[ 1375301-91-9 ]
(6-bromo-2-pyridyl)methyl N-carbamimidoylcarbamate [ No CAS ]
[6-(2-cyclopropylpyrimidin-5-yl)-2-pyridyl]methyl N-carbamimidoylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); In 1,4-dioxane; water; at 100.0℃; for 2.0h;	A mixture of 1.0 eq of intermediate 111.1, 1.1 eq intermediate IV.53, 3.0 eq K3PO4 and 0.07 eq XPhos Pd G2 in dioxane/water (ca. 5:1) are heated to 100C for 2 h. After cooling to RT the solvent is evaporated in taken up in a mixture of MeOH and DCM, filtered through a PL-thiol cartridge and evaporated. The crude product is purified by HPLC. ESI-MS: m/z = 313 (M+H)+, Rt(HPLC): 0.39 min (HPLC-B)

Reference： [1]Patent: WO2017/194453,2017,A1 .Location in patent: Page/Page column 59; 60

4
[ 304902-96-3 ]
[ 73183-34-3 ]
[ 1375301-91-9 ]

Yield	Reaction Conditions	Operation in experiment
39%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; at 90.0℃; for 16.0h;	A mixture of 12A(0.8 g, 4.02 mmol), Pd(dppf)C12 (147 mg, 0.20 mmol), KOAc (592 mg, 6.03 mmol) and bis(pinacolato)diboron (1.16 g, 4.82 mmol) in dioxane (20 mL) was heated to 90 C. overnight. After cooling, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (1/50 to 1/10 ethyl acetate/pet. ether) to give 12B (0.38 g, 39% yield) as a yellow solid: ESI mlz 247.1 [M+H].

Reference： [1]Patent: US2018/291002,2018,A1 .Location in patent: Paragraph 0427; 0429

5
[ 1375301-91-9 ]
C₁₇H₂₅BrN₄O [ No CAS ]
[ 76-05-1 ]
(x)C₂HF₃O₂*C₂₄H₃₂N₆O [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 10242 - 10254

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