[ CAS No. 14394-56-0 ] {[proInfo.proName]}

Name: 14394-56-0|4-Amino-6-chloro-5-methylpyrimidine|95%
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Quality Control of [ 14394-56-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 14394-56-0 ]

Product Details of [ 14394-56-0 ]

CAS No. :	14394-56-0	MDL No. :	MFCD09991585
Formula :	C₅H₆ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JCIGQYDCSFFHPI-UHFFFAOYSA-N
M.W :	143.57	Pubchem ID :	21934626
Synonyms :

Calculated chemistry of [ 14394-56-0 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.41
TPSA :	51.8 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	1.18
Log Po/w (WLOGP) :	1.03
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	1.31
Consensus Log Po/w :	1.05

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.97
Solubility :	1.55 mg/ml ; 0.0108 mol/l
Class :	Very soluble
Log S (Ali) :	-1.86
Solubility :	1.97 mg/ml ; 0.0137 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.27
Solubility :	0.766 mg/ml ; 0.00533 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.57

Safety of [ 14394-56-0 ]

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

Application In Synthesis of [ 14394-56-0 ]

* 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 [ 14394-56-0 ]
Downstream synthetic route of [ 14394-56-0 ]

[ 14394-56-0 ] Synthesis Path-Upstream 1~2

1
[ 4316-97-6 ]
[ 14394-56-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With ammonia In methanol at 140℃; for 0.666667 h;	A mixture of 4,6-dichloro-5-methylpyrimidine (available from Sigma-Aldrich No.595446) (5 g, 30.70 mmol) in ammonia (7 M solution in MeOH, 15 ml, 105 mmol) was left under stirring for 40 min in a sealed vial at 140 ⁰C. Water (300 ml) and EtOAc (600 ml) were added to the resulting white suspension and the two layers were separated. The aqueous phase was extracted with EtOAc (3 x 600 ml). The collected organic phases were dried (Na₂SO₄), filtered and concentrated under reduced pressure to give the title compound D3 (3.10 g, 20.73 mmol, 68percent yield) as a white solid. UPLC: rt = 0.41 min, peaks observed: 144 (M+l, 100percent) and 146 (M+ 1, 33percent). C₅H₆ClN₃ requires 143. ¹H NMR (400 MHz, DMSO- d₆) δ(ppm): 8.06 (s, 1 H), 7.09 (bs, 2 H), 2.07 (s, 3 H).

Reference： [1] Patent: WO2009/3997, 2009, A1, . Location in patent: Page/Page column 18
[2] Journal of the Chemical Society, 1947, p. 41,45

2
[ 63447-38-1 ]
[ 14394-56-0 ]

Reference： [1] Journal of the Chemical Society, 1947, p. 41,45

[ 14394-56-0 ] Synthesis Path-Downstream 1~11

3
[ 63447-38-1 ]
[ 14394-56-0 ]

Reference： [1]Journal of the Chemical Society,1947,p. 41,45

5
[ 14394-56-0 ]
[ 1097180-24-9 ]
[ 1097180-27-2 ]
C₁₈H₂₅ClN₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 80℃; for 4h;	To a solution of 1,1-dimethylethyl (25)-2-(3-bromo-2-oxopropyl)-l-piperidinecarboxylate D2 (3 g, 9.37 mmol) in DMF (25 ml) was added <strong>[14394-56-0]6-chloro-5-methyl-4-pyrimidinamine</strong> D3 (1.48 g, 10.31 mmol) and the resulting mixture was stirred at 80 0C for 4 h. The solvent was removed under reduced pressure and Et2O (300 ml) and water (200 ml) were added to the residue. The two layers were separated and the organic one was back-extracted with DCM (2 x 200 ml). The collected organic phases were dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (Biotage SP4 40 M, from DCM 100 to DCM /MeOH 95/5). Collected fractions gave a solid that was eluted through a SCX column to afford a crude material (1 g) containing the title compound <n="20"/>D4, the corresponding N-Boc protected derivative and some residual 6-chloro-5-methyl-4- pyrimidinamine. [N-Boc derivative data. UPLC: rt = 0.74 min, peaks observed: 365 (M+l, 100%) and 367 (M+l, 33%). C18H25ClN4O2 requires 364]. The crude was dissolved in DCM (10 ml) and the resulting solution cooled down to 0 0C. TFA (2.50 ml) was added and the reaction left under stirring for 4 h at room temperature. Volatiles were removed under reduced pressure and the residue eluted through a SCX column (50 g) to afford the title compound D4 (0.80 g) contaminated with some residual 6-chloro-5-methyl-4- pyrimidinamine. HPLC (walk-up): rt = 2.44 min. UPLC: rt = 0.41 min, peaks observed: 265 (M+l, 100%) and 267 (M+l, 33%). C13H17ClN4 requires 264.

Reference： [1]Patent: WO2009/3997,2009,A1 .Location in patent: Page/Page column 19-20

6
[ 14394-56-0 ]
[ 6640-24-0 ]
[ 1366472-44-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2283 - 2286

7
[ 14394-56-0 ]
1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine [ No CAS ]
5-methyl-4-N-{1-[3-(pyridin-2-yl)indolizin-2-yl]ethyl}pyrimidine-4,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.0207 g	With N-ethyl-N,N-diisopropylamine; In tert-butyl alcohol; at 130 - 150℃; for 240h;Reflux;	Example 50 5-methyl-4-N-{1-[3-(pyridin-2-yl)indolizin-2-yl]ethyl}pyrimidine-4,6-diamine To a solution of 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.100 g, 0.42 mmol) in t-BuOH (4.5 mL), <strong>[14394-56-0]6-chloro-5-methylpyrimidin-4-amine</strong> (0.060 g, 0.42 mmol) was added followed by DIPEA (0.146 mL, 0.84 mmol) and the resulting mixture was heated to reflux for 24 h. Additional 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.100 g, 0.42 mmol) was added over 48 h heating to reflux. The solvent was removed and the crude was dissolved in n-BuOH (4.5 mL); DIPEA (0.146 mL, 0.84 mmol) was added and the reaction was heated to 130 C. for 10 days. An additional experiment was performed: to a solution of 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.059 g, 0.25 mmol) in n-BuOH (2.7 mL), <strong>[14394-56-0]6-chloro-5-methylpyrimidin-4-amine</strong> (0.036 g, 0.25 mmol) was added followed by DIPEA (0.087 mL, 0.50 mmol) and the resulting mixture was heated under MW irradiation for 2 h at 120 C. and for 2 h at 150 C. Then the mixture was heated under thermal conditions at 130 C. for 24 h. Additional 1-[3-(pyridin-2-yl)indolizin-2-yl]ethan-1-amine Q2 (0.059 g, 0.25 mmol) was added over 10 days continuing the heating at 130 C. The two reaction mixtures were combined, the solvent was removed and the crude was partitioned between DCM/MeOH 4/1 and water. The organic phase was dried over sodium sulfate, the solvent was removed under reduced pressure and the crude was purified by flash chromatography on Biotage silica-NH cartridge (cyclohexane:EtOAc=50:50 to 40:60); two further purifications by flash chromatography on Biotage silica cartridge (DCM to DCM:MeOH=98:2) were required to afford title compound as a dark yellow solid (0.0207 g). MS/ESI+ 345.2 [MH]+, Rt 0.56 min (Method A). 1H NMR (400 MHz, DMSO-d6) delta ppm 8.78 (d, 1H), 8.69-8.74 (m, 1H), 7.80-7.92 (m, 2H), 7.77 (s, 1H), 7.46 (d, 1H), 7.27-7.35 (m, 1H), 6.76-6.83 (m, 1H), 6.67 (s, 1H), 6.54-6.61 (m, 1H), 6.24-6.33 (m, 1H), 5.85 (br. s., 2H), 5.60-5.70 (m, 1H), 1.80 (s, 3H), 1.41 (d, 3H).

Reference： [1]Patent: US2015/361100,2015,A1 .Location in patent: Paragraph 0997; 0998; 0999

8
[ 14394-56-0 ]
[ 14215-97-5 ]
(2R,3R,4R,5R)-2-((6-amino-5-methylpyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 5881 - 5889

9
[ 14394-56-0 ]
5-((6-(cyclopropanoylamino)-5-methylpyrimidin-4-yl)amino)-6-methoxy-1H-indazole [ No CAS ]

Reference： [1]Patent: CN109020957,2018,A

10
[ 14394-56-0 ]
1-((2-(trimethylsilyl)ethoxy)methyl)-5-((6-(cyclopropanoylamino)-5-methylpyrimidin-4-yl)amino)-6-methoxyindazole [ No CAS ]

Reference： [1]Patent: CN109020957,2018,A

11
[ 14394-56-0 ]
[ 4023-34-1 ]
N-(6-chloro-5-methylpyrimidin-4-yl)cyclopropanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With pyridine; In tetrahydrofuran; at 60℃; for 16h;Inert atmosphere;	The compound <strong>[14394-56-0]6-chloro-5-methylpyrimidin-4-amine</strong> 48a (100 mg, 0.700 mmol), cyclopropylcarbonyl chloride (87 mg,0.839 mmol), pyridine (3 mL) and tetrahydrofuran (3 mL) were combined.The mixture was heated to 60 C and stirred for 16 hours.This mixture was diluted with 20 ml of water and extracted with ethyl acetate (20 mL×2).The combined organic phases were washed with brine (20 mL×2).The organic phase is dried over anhydrous sodium sulfate, and the desiccant is removed by filtration.Decompressing under reduced pressure to obtain a crude product,The residue was purified by preparative silica gel ( petroleum ether / ethyl acetate = 4:1).The target product N-(6-chloro-5-methylpyrimidin-4-yl)cyclopropanecarboxamide 48b (40 mg,0.190 mmol, white solid). Yield: 27%.

Reference： [1]Patent: CN109020957,2018,A .Location in patent: Paragraph 0207

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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
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P270	Do not eat, drink or smoke when using this product.
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P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
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P314	Get medical advice/attention if you feel unwell.
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P320
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P321
P322
P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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.
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
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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
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H228	Flammable solid
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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. 14394-56-0 ] {[proInfo.proName]}

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Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 14394-56-0 ]

[ 14394-56-0 ] Synthesis Path-Upstream 1~2

[ 14394-56-0 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 14394-56-0 ]

Chlorides

Amines

Related Parent Nucleus of [ 14394-56-0 ]

Pyrimidines

Precautionary Statements-General

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Response

Storage

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Health hazards

Environmental hazards

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[ 14394-56-0 ]

Related Parent Nucleus of
[ 14394-56-0 ]