[ CAS No. 2305-87-5 ] {[proInfo.proName]}

Name: 2305-87-5|4-Phenylpyrimidin-2-amine|98%
Brand: Ambeed
SKU: A457418
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COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 2305-87-5 ]

CAS No. :	2305-87-5	MDL No. :	MFCD00094706
Formula :	C₁₀H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DMEGQEWPMXDRMO-UHFFFAOYSA-N
M.W :	171.20	Pubchem ID :	598777
Synonyms :

Calculated chemistry of [ 2305-87-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.87
TPSA :	51.8 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) :	-6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.52
Log Po/w (WLOGP) :	1.73
Log Po/w (MLOGP) :	1.11
Log Po/w (SILICOS-IT) :	1.77
Consensus Log Po/w :	1.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.572 mg/ml ; 0.00334 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	1.04 mg/ml ; 0.00608 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.81
Solubility :	0.0268 mg/ml ; 0.000157 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 2305-87-5 ]

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

Application In Synthesis of [ 2305-87-5 ]

* 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 [ 2305-87-5 ]
Downstream synthetic route of [ 2305-87-5 ]

[ 2305-87-5 ] Synthesis Path-Upstream 1~6

1
[ 2305-87-5 ]
[ 38675-31-9 ]

Reference： [1] Journal of the Chemical Society, 1951, p. 2323,2327

2
[ 2305-87-5 ]
[ 13036-50-5 ]
[ 38675-31-9 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 91 - 94[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 1, p. 102 - 106

3
[ 2305-87-5 ]
[ 13036-50-5 ]

Reference： [1] Journal of the Chemical Society, 1951, p. 2323,2327

4
[ 2305-87-5 ]
[ 13036-50-5 ]
[ 38675-31-9 ]
[ 85658-55-5 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 91 - 94[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 1, p. 102 - 106

5
[ 2305-87-5 ]
[ 85658-55-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With N-Bromosuccinimide In acetonitrile at 20℃; for 20 h;	To a 100 mL round bottom flask, were added 4-phenylpyrimidin-2-amine (0.4 g, 0.0023 mol) and mixture of acetonitrile and chloroform (1 : 1, 20 mL). To the same flask N- bromosuccinimide (0.499 g, 0,0028 mol) was added. The reaction mixture was stirred at room temperature for 20 h. The solvent was removed under reduced pressure to get the residue. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to get the crude product. The crude product was purified by column chromatography using 60 - 120 silica gel and 40 percent ethyl acetate in hexane to get the title compound [0.3 g, 51 percent]. ^{FontWeight="Bold" FontSize="10"}H NMR (300 MHz, DMSO-J₆): δ 8.43 (s, 1H), 7.65-7.61 (m, 2H), 7.49-7.42 (m, 3H), 6.97 (brs, 2H); LC-MS: 251.9 [M+2H]⁺.
45%	With bromine In acetic acid at 20 - 45℃; for 3 h;	Compound 47 (0.30 g, 1.75 mmol) was dissolved in glacial acetic acid (15 ml) and warmed to 45° C. Br₂ (0.09 mL, 1.75 mmol) was added slowly. The resulting mixture was then allowed to stir at room temperature for 3 h. The solvent was removed under vacuum to a solid residue. This was then transferred onto a filter funnel and washed with DCM, followed by water. The remaining solid was then dried under high vacuum for 16 h to give 197 mg of 13 (45percent) as a pale yellow solid: ¹H NMR (400 MHz, d₆-DMSO)δ 8.40 (s, 1H), 7.61 (m, 2H), 7.45 (m, 3H), 6.96 (s, 2H); MS (+)-ES [M]⁺250.0 [M+2]⁺252.0 m/z. Elemental analysis for C₁₀H₈BrN₃: calc'd: C, 48.02; H, 3.22; Br, 31.95; N, 16.80; found: C, 47.91; H, 3.28; Br, 32.15; N, 16.80.

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 91 - 94[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 1, p. 102 - 106
[3] Patent: WO2014/125426, 2014, A1, . Location in patent: Page/Page column 55; 56
[4] Patent: US2005/54590, 2005, A1, . Location in patent: Page/Page column 41

6
[ 2305-87-5 ]
[ 13036-50-5 ]
[ 38675-31-9 ]
[ 85658-55-5 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 91 - 94[2] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 1, p. 102 - 106

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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Deprotonation of Methylbenzene • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nitrosation of Amines • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Preparation of LDA • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Ugi Reaction • Vilsmeier-Haack Reaction

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[ 2305-87-5 ]

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Yield	Reaction Conditions	Operation in experiment
55%	With sulfuric acid; hydrogen bromide; urea; sodium nitrite at 0 - 5℃; for 1h;
51%	With N-Bromosuccinimide In acetonitrile at 20℃; for 20h;	28.iii Step iii: 5-bromo-4-phenylpyrimidin-2-amine To a 100 mL round bottom flask, were added 4-phenylpyrimidin-2-amine (0.4 g, 0.0023 mol) and mixture of acetonitrile and chloroform (1 : 1, 20 mL). To the same flask N- bromosuccinimide (0.499 g, 0,0028 mol) was added. The reaction mixture was stirred at room temperature for 20 h. The solvent was removed under reduced pressure to get the residue. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to get the crude product. The crude product was purified by column chromatography using 60 - 120 silica gel and 40 % ethyl acetate in hexane to get the title compound [0.3 g, 51 %]. FontWeight="Bold" FontSize="10" H NMR (300 MHz, DMSO-J6): δ 8.43 (s, 1H), 7.65-7.61 (m, 2H), 7.49-7.42 (m, 3H), 6.97 (brs, 2H); LC-MS: 251.9 [M+2H]+.
45%	With bromine In acetic acid at 20 - 45℃; for 3h;	5.2 Compound 47 (0.30 g, 1.75 mmol) was dissolved in glacial acetic acid (15 ml) and warmed to 45° C. Br2 (0.09 mL, 1.75 mmol) was added slowly. The resulting mixture was then allowed to stir at room temperature for 3 h. The solvent was removed under vacuum to a solid residue. This was then transferred onto a filter funnel and washed with DCM, followed by water. The remaining solid was then dried under high vacuum for 16 h to give 197 mg of 13 (45%) as a pale yellow solid: 1H NMR (400 MHz, d6-DMSO)δ 8.40 (s, 1H), 7.61 (m, 2H), 7.45 (m, 3H), 6.96 (s, 2H); MS (+)-ES [M]+250.0 [M+2]+252.0 m/z. Elemental analysis for C10H8BrN3: calc'd: C, 48.02; H, 3.22; Br, 31.95; N, 16.80; found: C, 47.91; H, 3.28; Br, 32.15; N, 16.80.

Yield	Reaction Conditions	Operation in experiment
84%	With sodium ethanolate In ethanol for 20h; Reflux;
61%	With sodium ethanolate In ethanol for 20h; Reflux;	28.ii Step ii: 4-phenylpyrimidin-2-amine To a 100 mL round bottom flask, were added 3-(dimethylamino)-l-phenylprop-2-en-l- one (1.0 g, 0.0057 mol) and ethanol (30 mL). To the same flask, guanidine hydrochloride (1.08 g, 0.0114 mol) and NaOEt (2.0 M in ethanol, 0.77 g, 0.0114 mol) were added. The reaction mixture was stirred at reflux temperature for 20 h. The ethanol was removed under reduced pressure to get the residue. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get the crude product. The crude product was purified by column chromatography using 60 - 120 silica gel and 60 % ethyl acetate in hexane to get the title compound [0.6 g, 61 %]. FontWeight="Bold" FontSize="10" H NMR (300 MHz, DMSO-J6): δ 8.31 (d, = 5.1 Hz, 1H), 8.07-8.04 (m, 2H), 7.50-7.48 (m, 3H), 7.13 (d, = 5.1 Hz, 1H), 6.67 (brs, 2H); LC-MS: 171.9 [M+H]+.
	With sodium hydroxide In ethanol for 0.2h; Reflux;

	Multi-step reaction with 2 steps 1: 20 h / 115 °C 2: potassium etoxide / ethanol / 20 h / Reflux
	Multi-step reaction with 2 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux 2: sodium hydroxide / ethanol / 0.2 h / Reflux
	Multi-step reaction with 2 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 48 h / 120 °C 2: butan-1-ol / 12 h / Reflux
	Multi-step reaction with 2 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 48 h / Reflux 2: sodium hydroxide / butan-1-ol / 12 h / Reflux
	Multi-step reaction with 2 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 48 h / 120 °C 2: potassium carbonate / butan-1-ol / 12 h / 120 °C

Yield	Reaction Conditions	Operation in experiment
76.5%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 20 - 100℃; for 20h; Inert atmosphere; Schlenk technique;
31%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 120℃; for 15h; Inert atmosphere; Reflux;

[ CAS No. 2305-87-5 ] {[proInfo.proName]}

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