[ CAS No. 206564-00-3 ] {[proInfo.proName]}

Name: 206564-00-3|4-(2-Furyl)pyrimidin-2-amine|95%
Brand: Ambeed
SKU: A152406
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Quality Control of [ 206564-00-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 206564-00-3 ]

Product Details of [ 206564-00-3 ]

CAS No. :	206564-00-3	MDL No. :	MFCD01940445
Formula :	C₈H₇N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JTOGGBLTIHXWEH-UHFFFAOYSA-N
M.W :	161.16	Pubchem ID :	3804989
Synonyms :

Calculated chemistry of [ 206564-00-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.14
TPSA :	64.94 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	0.62
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	-0.32
Log Po/w (SILICOS-IT) :	1.22
Consensus Log Po/w :	0.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.32 mg/ml ; 0.0144 mol/l
Class :	Very soluble
Log S (Ali) :	-1.56
Solubility :	4.46 mg/ml ; 0.0276 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.01
Solubility :	0.156 mg/ml ; 0.000971 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.35

Safety of [ 206564-00-3 ]

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 [ 206564-00-3 ]

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

Upstream synthesis route of [ 206564-00-3 ]
Downstream synthetic route of [ 206564-00-3 ]

[ 206564-00-3 ] Synthesis Path-Upstream 1~8

1
[ 50-01-1 ]
[ 17168-45-5 ]
[ 206564-00-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 100℃; for 21 h;	A suspension of 3-(dimethylamino)-1-(2-furyl)-2-propen-1-one (5.0 g, 30.3 mmol), guanidine hydrochloride (5.8 g, 60.7 mmol) and potassium carbonate (8.4 g, 60.9 mmol) in N, N-dimethylformamide (50 ml) was stirred at 100°C for 21 hours. After cooling as it was, the reaction mixture was diluted with ice water (250 ml). The resulting solid was collected by filtration and washed with water, to give the title compound (4.19 g, 86percent) as a pale brown solid.1H NMR (400 MHz, DMSO-d6) δ ppm; 6.66 (2H, br s), 6.68 (1H, dd, J = 2.0, 3.2 Hz), 6.88 (1H, d, J = 5.2 Hz), 7.17 (1H, dd, J = 0.8, 3.2 Hz), 7.88 (1H, dd, J = 0.8, 2.0 Hz), 8.28 (1H, d, J = 5.2 Hz); MS m/e (ESI) 162 (MH+).

Reference： [1] Patent: EP1439175, 2004, A1, . Location in patent: Page 46

2
[ 593-85-1 ]
[ 206564-00-3 ]

Reference： [1] Heterocycles, 1998, vol. 47, # 2, p. 689 - 702

3
[ 506-93-4 ]
[ 17168-45-5 ]
[ 206564-00-3 ]

Reference： [1] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495

4
[ 37176-67-3 ]
[ 50-01-1 ]
[ 206564-00-3 ]

Reference： [1] Green Chemistry, 2011, vol. 13, # 11, p. 3238 - 3247

5
[ 1192-62-7 ]
[ 206564-00-3 ]

Reference： [1] Heterocycles, 1998, vol. 47, # 2, p. 689 - 702
[2] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495

6
[ 109482-86-2 ]
[ 206564-00-3 ]

Reference： [1] Heterocycles, 1998, vol. 47, # 2, p. 689 - 702

7
[ 527-69-5 ]
[ 206564-00-3 ]

Reference： [1] Green Chemistry, 2011, vol. 13, # 11, p. 3238 - 3247

8
[ 1205744-94-0 ]
[ 206564-00-3 ]

Reference： [1] Synthesis, 2009, # 21, p. 3617 - 3632

[ 206564-00-3 ] Synthesis Path-Downstream 1~32

1
[ 593-85-1 ]
2-(2-furyl)-1,1,5,5-tetramethyl-1,5-diazapentadienium hexafluorophosphate [ No CAS ]
[ 206564-00-3 ]

Reference： [1]Heterocycles,1998,vol. 47,p. 689 - 702

2
[ 1192-62-7 ]
[ 206564-00-3 ]

Reference： [1]Heterocycles,1998,vol. 47,p. 689 - 702
[2]Organic Process Research and Development,2008,vol. 12,p. 490 - 495
[3]Chinese Chemical Letters,2019,vol. 30,p. 2160 - 2162

3
[ 109482-86-2 ]
[ 206564-00-3 ]

Reference： [1]Heterocycles,1998,vol. 47,p. 689 - 702

4
3-chloro-3-(2-furyl)prop-2-en-1-ylidenedimethyliminium hexafluorophosphate [ No CAS ]
[ 206564-00-3 ]

Reference： [1]Heterocycles,1998,vol. 47,p. 689 - 702

5
[ 50-01-1 ]
[ 17168-45-5 ]
[ 206564-00-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 100℃; for 21.0h;	A suspension of 3-(dimethylamino)-1-(2-furyl)-2-propen-1-one (5.0 g, 30.3 mmol), guanidine hydrochloride (5.8 g, 60.7 mmol) and potassium carbonate (8.4 g, 60.9 mmol) in N, N-dimethylformamide (50 ml) was stirred at 100C for 21 hours. After cooling as it was, the reaction mixture was diluted with ice water (250 ml). The resulting solid was collected by filtration and washed with water, to give the title compound (4.19 g, 86%) as a pale brown solid.1H NMR (400 MHz, DMSO-d6) delta ppm; 6.66 (2H, br s), 6.68 (1H, dd, J = 2.0, 3.2 Hz), 6.88 (1H, d, J = 5.2 Hz), 7.17 (1H, dd, J = 0.8, 3.2 Hz), 7.88 (1H, dd, J = 0.8, 2.0 Hz), 8.28 (1H, d, J = 5.2 Hz); MS m/e (ESI) 162 (MH+).
	With sodium ethanolate; In ethanol; at 20℃;	General procedure: The N, N-Dimethylformamide dimethyl acetal (1.0 equiv) and different aromatic ethanones (1a-1c, 1.0 equiv) in dry toluene and the reaction mixture was heated to reflux for 4 h. The solvent was removed under reduced pressure to give the residue (2a-2c). Then, a solution of guanidine hydrochloride (1.0 equiv) and sodium ethoxide (1.0 equiv) in ethanol was added to the residue, stirred at room temperature overnight. The solvent was removed by distillation, and the residue was subjected to column chromatography which was eluted by ethyl acetate in petroleum ether to obtain compounds 3a-3c as solid.

Reference： [1]Patent: EP1439175,2004,A1 .Location in patent: Page 46
[2]Chinese Chemical Letters,2019,vol. 30,p. 2160 - 2162

6
[ 206564-00-3 ]
[ 357285-97-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-Bromosuccinimide; In DMF (N,N-dimethyl-formamide); at 2℃; for 6.0h;	To a solution of 4-(2-furyl)-2-pyrimidinylamine (4.10 g, 25.4 mmol) in N,N-dimethylformamide (40 ml) was added N-bromosuccinimide (4.53 g, 25.5 mmol) at 2C, followed by stirring as it was. After 6 hours, the reaction mixture was diluted with an aqueous saturated sodium bicarbonate solution (240 ml). The mixture was ice-cooled, and then the crystals were collected by filtration and washed with water, to give the title compound (5.10 g, 84%) as a pale brown solid.1H NMR (400 MHz, DMSO-d6) delta ppm; 6.73 (1H, dd, J = 1.6, 3.6 Hz), 6.96 (2H, br s), 7.50 (1H, dd, J = 0.8, 3.6 Hz), 7.97 (1H, dd, J = 0.8, 1.6 Hz), 8.41 (1H, s).
81.4%	With N-Bromosuccinimide; dibenzoyl peroxide; In acetonitrile; at 80℃; for 6.0h;	General procedure: 4-p-Tolylpyrimidin-2-amine (3a) (1.0 equiv), N-chlorosuccinimide (1.1 equiv) and benzoyl peroxide (0.2 equiv) were dissolved in acetonitrile and stirred at 80 C for 6 h. The reaction mixture was cooled to room temperature, then the solvent was removed in vacuo. The crude product was purified by silica gel column with acetone/petroleum ether (v/v, 1:5) as eluent to obtain 4a. Using the same procedure described above for the other compounds exception of 6a-6c under a lower reaction temperature (40 C).

Reference： [1]Patent: EP1439175,2004,A1 .Location in patent: Page 46
[2]Chinese Chemical Letters,2019,vol. 30,p. 2160 - 2162

7
[ 1205744-94-0 ]
[ 206564-00-3 ]

Reference： [1]Synthesis,2009,p. 3617 - 3632

8
[ 527-69-5 ]
[ 206564-00-3 ]

Reference： [1]Green Chemistry,2011,vol. 13,p. 3238 - 3247

9
[ 37176-67-3 ]
[ 50-01-1 ]
[ 206564-00-3 ]

Reference： [1]Green Chemistry,2011,vol. 13,p. 3238 - 3247

10
[ 506-93-4 ]
[ 17168-45-5 ]
[ 206564-00-3 ]

Reference： [1]Organic Process Research and Development,2008,vol. 12,p. 490 - 495

11
[ 206564-00-3 ]
N-(3-(4-(furan-2-yl)pyrimidin-2-ylamino)-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide [ No CAS ]

Reference： [1]Organic Process Research and Development,2008,vol. 12,p. 490 - 495

12
[ 206564-00-3 ]
C₂₃H₁₉ClN₄O₂ [ No CAS ]

Reference： [1]Organic Process Research and Development,2008,vol. 12,p. 490 - 495

13
[ 206564-00-3 ]
C₁₅H₁₄N₄O [ No CAS ]

Reference： [1]Organic Process Research and Development,2008,vol. 12,p. 490 - 495

14
[ 7745-93-9 ]
[ 206564-00-3 ]
C₁₅H₁₂N₄O₃ [ No CAS ]