[ CAS No. 22387-37-7 ] {[proInfo.proName]}

Name: 22387-37-7|8-Methyl-7H-purin-6-amine|98%
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SKU: A161222
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3d Animation Molecule Structure of 22387-37-7

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Quality Control of [ 22387-37-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 22387-37-7 ]

SDS Specification

Alternatived Products of [ 22387-37-7 ]

Product Details of [ 22387-37-7 ]

CAS No. :	22387-37-7	MDL No. :	MFCD19237006
Formula :	C₆H₇N₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ORUIZIXJCCIGAI-UHFFFAOYSA-N
M.W :	149.15	Pubchem ID :	95187
Synonyms :

Calculated chemistry of [ 22387-37-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.17
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	41.05
TPSA :	80.48 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) :	-6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.17
Log Po/w (XLOGP3) :	1.05
Log Po/w (WLOGP) :	0.25
Log Po/w (MLOGP) :	-0.44
Log Po/w (SILICOS-IT) :	0.81
Consensus Log Po/w :	0.37

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.03
Solubility :	1.39 mg/ml ; 0.0093 mol/l
Class :	Soluble
Log S (Ali) :	-2.33
Solubility :	0.696 mg/ml ; 0.00467 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.17
Solubility :	0.997 mg/ml ; 0.00668 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 22387-37-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22387-37-7 ]

* 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 [ 22387-37-7 ]
Downstream synthetic route of [ 22387-37-7 ]

[ 22387-37-7 ] Synthesis Path-Upstream 1~6

1
[ 29767-70-2 ]
[ 118-70-7 ]
[ 66224-66-6 ]
[ 22387-37-7 ]

Reference： [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 10, p. 707 - 712

2
[ 60-35-5 ]
[ 49721-45-1 ]
[ 22387-37-7 ]

Yield	Reaction Conditions	Operation in experiment
11%	at 240℃; for 6 h;	Example 109; Synthesis of 2- (6-Arnino-8-methyl-vurin-9-yl)-5-hydroxMeLhyl-tetrahvdro- furan-3, 4-diol; Step 1; Synthesis of 8-Methyl-9H-purin-6-ylamine; 4,5, 6-Triaminopyrimidine sulfate (3. 0g, 13.4mmol) and acetamide (l. Og, 16. 9mmol) were added to a 25mL autoclave bomb and heated to 240°C for 6 hours. The crude product was then boiled in H20 for 1 hour and filtered through a small pad of Celite. The flow through was concentrated and purified by HPLC 0-10percent Buffer B over 30min at a flow rate of lOmLs/min. Buffer A-0. 1percent triethylammonium acetate in water, Buffer B-0. 1 percent triethylammonium acetate in CH3CN. Pooled the appropriate fractions and concentrated in vacuo to give 225mg (11 percent) of the title compound.

Reference： [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 8, p. 2073 - 2080
[2] Patent: WO2003/93290, 2003, A2, . Location in patent: Page/Page column 131-132

3
[ 713140-78-4 ]
[ 22387-37-7 ]

Reference： [1] Synthesis, 2004, # 6, p. 889 - 894

4
[ 218431-07-3 ]
[ 22387-37-7 ]

Reference： [1] Synthesis, 2004, # 6, p. 889 - 894

5
[ 239784-24-8 ]
[ 22387-37-7 ]

Reference： [1] Synthesis, 2004, # 6, p. 889 - 894

6
[ 29767-70-2 ]
[ 118-70-7 ]
[ 66224-66-6 ]
[ 22387-37-7 ]

Reference： [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 10, p. 707 - 712

[ 22387-37-7 ] Synthesis Path-Downstream 1~16

1
[ 108-24-7 ]
[ 118-70-7 ]
[ 22387-37-7 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 1457,1458

2
[ 60-35-5 ]
[ 49721-45-1 ]
[ 22387-37-7 ]

Yield	Reaction Conditions	Operation in experiment
11%	at 240℃; for 6.0h;	Example 109; Synthesis of 2- (6-Arnino-8-methyl-vurin-9-yl)-5-hydroxMeLhyl-tetrahvdro- furan-3, 4-diol; Step 1; Synthesis of 8-Methyl-9H-purin-6-ylamine; 4,5, 6-Triaminopyrimidine sulfate (3. 0g, 13.4mmol) and acetamide (l. Og, 16. 9mmol) were added to a 25mL autoclave bomb and heated to 240C for 6 hours. The crude product was then boiled in H20 for 1 hour and filtered through a small pad of Celite. The flow through was concentrated and purified by HPLC 0-10% Buffer B over 30min at a flow rate of lOmLs/min. Buffer A-0. 1% triethylammonium acetate in water, Buffer B-0. 1 % triethylammonium acetate in CH3CN. Pooled the appropriate fractions and concentrated in vacuo to give 225mg (11 %) of the title compound.

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2073 - 2080
[2]Patent: WO2003/93290,2003,A2 .Location in patent: Page/Page column 131-132

3
[ 29767-70-2 ]
[ 118-70-7 ]
[ 66224-66-6 ]
[ 22387-37-7 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1982,vol. 36,p. 707 - 712

6
[ 713140-78-4 ]
[ 22387-37-7 ]

Reference： [1]Synthesis,2004,p. 889 - 894

7
[ 218431-07-3 ]
[ 22387-37-7 ]

Reference： [1]Synthesis,2004,p. 889 - 894

8
[ 239784-24-8 ]
[ 22387-37-7 ]

Reference： [1]Synthesis,2004,p. 889 - 894

9
[ 4637-24-5 ]
[ 22387-37-7 ]
[ 622380-03-4 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; for 24.0h;Heating / reflux;	Step 2; Synthesis of N, N-Dimethyl-N'- (8-methyl-9H-purin-6-yl)-formamidine; To a suspension of the product in Step 1 above (225mg, 1. 5 lmmol) in MeOH (14mL) and methylene chloride (7mL) was added N'N'-dimethylformamide dimethyl acetal (0. 8mL, 4. 52mmol) and the mixture heated to reflux for 24 hours. The resuling yellow solution was concentrated in vacuo to a yellow oil. This oil was co- evaporated with methylene chloride (2 x 15mL) and held under high vacuum for 2hours. The crude product was used directly in Step 3, without further purification.

Reference： [1]Patent: WO2003/93290,2003,A2 .Location in patent: Page/Page column 132

10
[ 503543-44-0 ]
[ 22387-37-7 ]
9-(2,3-di-O-acetyl-5-O-benzoyl-4-C-methyl-β-D-ribofuranosyl)-8-methyl adenine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tin(IV) chloride; In acetonitrile; at 20.0℃;	dry acetonitrile (50 mL) solution of 7 (1.10g,2.79mmol) was treated with 8-methyl adenine and stannic chloride (SnCl4,660L,5.58mmol), and stirred at room temperature overnight. The solution wasconcentrated under reduced pressure, and diluted with chloroform (100 mL), andtreated with cold saturated aqueous NaHCO3 solution (100 mL). Themixture was filtered through Celite and the precipitate was washed with hot chloroform.The combined filtrates were washed with water (100 mL) and brine (100 mL), and dried(Na2SO4), and evaporated under reduced pressure. Theresidue was purified by silica gel column chromatography [eluent: methanol (3%to 5%) / step gradient of methylene chloride] to give 20

Reference： [1]Patent: JP2015/205885,2015,A .Location in patent: Paragraph 0461

11
[ 503543-44-0 ]
[ 22387-37-7 ]
9-(4-C-methyl-β-D-ribofuranosyl)-8-methyladenine [ No CAS ]

Reference： [1]Patent: JP2015/205885,2015,A

12
(1R,3S)-methyl 3-(methylsulfonyloxy)cyclopentanecarboxylate [ No CAS ]
[ 22387-37-7 ]
(1R,3R)-methyl 3-(6-amino-8-methyl-9H-purin-9-yl)cyclopentanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.2%	With caesium carbonate; In N,N-dimethyl-formamide; at 80.0℃; for 5.0h;	Example 16-Preparation of (1R,3R)-methyl 3-(6-amino-8-methyl-9H-purin-9-yl)cyclopentanecarboxylate (Compound 9o) <strong>[22387-37-7]8-Methyladenin</strong>e (compound 80o, 200 mg, 1.3409 mmoles) and compound 5 (387 mg, 1.743 mmoles) were dissolved in anhydrous N,N-dimethylformamide (5 mL) and cesium carbonate (437 mg, 1.3409 mmoles) was added. The resulting mixture was stirred at 80 deg C. for 5 hours. After cooling to room temperature, the mixture was filtered and concentrated to dryness. Purification on basic alumina (1% methanol in dichloromethane) gave compound 9o (130 mg, 35.2% yield) as an off-white solid. 1HNMR (500 MHz, DMSO-d6) delta ppm: 8.1 (s, 1H), 7.0 (brs, 2H), 4.9 (m, 1H), 3.7-3.6 (s, 6H), 3.2 (m, 1H), 2.4-2.2 (m, 6H): Mass (m/z): 276.5 (M+H).

Reference： [1]Patent: US2017/362235,2017,A1 .Location in patent: Paragraph 0237; 0238

13
(1R,3S)-methyl 3-(methylsulfonyloxy)cyclopentanecarboxylate [ No CAS ]
[ 22387-37-7 ]
(1R,3R)-3-(6-amino-8-methyl-9H-purin-9-yl)-N-hydroxycyclopentanecarboxamide [ No CAS ]

Reference： [1]Patent: US2017/362235,2017,A1

14
[ 60410-16-4 ]
[ 22387-37-7 ]
C₁₁H₁₃N₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: 8-methyladenine With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine In tetrahydrofuran; dimethyl sulfoxide at 50℃; for 48h;	(1S,2R,3S,4R)-4-(6-Amino-8-methyl-9H-purin-9-yl)cyclopentane-1,2,3-triol (1d). To a solution of 8-methyladenine13 (319 mg, 2.1 mmol) in DMSO (5 mL) was added NaH (2.1 mmol). After the mixture was stirred at room temperature for 0.5 h, Pd(PPh3)4 (228 mg, 0.2 mmol), triphenylphosphine (78.6 mg, 0.3 mmol) and 15 (426 mg, 3.0 mmol) in THF (20 mL) was added. The resulting mixture was then stirred at 50 °C for 48 h and evaporated to dryness. The black residue was treated with H2O (10 mL) and extracted with EtOAc (2 15 mL). The combined organic layers were dried (anhydrous Na2SO4), filtered and the filtrate concentrated under reduced pressure. The resultant residue was purified by column chromatography (MeOH-CH2Cl2, 1:10) to give a white solid (320 mg, 48%), which was assumed to be 16 and was used directly in next reaction. To an ice-H2O cooled solution of the above solid (320 mg, 1.42 mmol) in THF/H2O (20 mL, 10:1) was added N-methylmorpholine N-oxide (0.6 mL, 50% aqueous) and osmium tetroxide (20 mg). This mixture was then stirred at room temperature for 24 h and the solvent removed under reduced pressure. Purification of the residue by column chromatography (MeOH-EtOAc, 4:1) provided 1d as a white solid (260 mg, 70%), which was purified by recrystalization from MeOH and hexanes, mp >250 °C (dec.). The NMR data agree with reported value.5 Anal. Calcd for C11H15N5O3·0.58 H2O: C, 47.87; H, 5.86; N, 25.38. Found: C, 48.26; H, 5.74; N, 24.99. EI-MS [M]+ Calcd: 265.1175; Found: 265.1175.

Reference： [1]Yin, Xueqiang; Chen, Qi; Ye, Wei; Li, Chong; Schneller, Stewart W. [Heterocycles, 2017, vol. 95, # 1, p. 445 - 461]

15
[ 2014-83-7 ]
[ 22387-37-7 ]
3-(2,6-dichloro-benzyl)-8-methyl-3H-purin-6-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%	In N,N-dimethyl-formamide; at 85.0℃;	A mixture of <strong>[22387-37-7]8-methyl-9H-purin-6-ylamine</strong> (150 mg, 1.0 mmol) and l,3-dichloro-2- chloromethyl-benzene (214 mg, 1.1 mmol) in DMF (3 mL) was stirred at 85 C overnight. The mixture was cooled and filtered. The filtrate was purified by prep-HPLC (NH4HCO3 system) to give 3-(2,6-dichloro-benzyl)-8-methyl-3H-purin-6-ylamine (2 mg, yield: 5 %) as white solid. 1H NMR (400 MHz, DMSO- d): d = 7.82 (s, 1H), 7.70 (brs, 2H), 7.60-7.58 (m, 2H), 7.51-7.47 (m, 1H), 5.67 (s, 2H), 2.38 (s, 3H). MS: m/z 308.0 (M+H+).

Reference： [1]Patent: WO2019/136093,2019,A1 .Location in patent: Paragraph 00257

16
[ 13061-96-6 ]
[ 6974-78-3 ]
[ 22387-37-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 95℃;Inert atmosphere;	A flask charged with 8-bromo-9H-purin-6-ylamine (500 mg, 2.3 mmol), methylboronic (200 mg, 3.5mmol), Pd(dppf)Cl2 (84 mg, 0.115 mmol) and K2C03 (938 mg, 0.9 mmol) in dioxane/H20 (50 mL/l0 mL) was degassed and filled with N2. The mixture was stirred at 95 C overnight. Solvent was removed and the residue was purified with prep-TLC (DCM/MeOH = 10/1) to give 8-methyl-9H-purin-6-ylamine (150 mg, yield: 43 %) as yellow solid. MS: m/z 150.0 (M+H+).

Reference： [1]Patent: WO2019/136093,2019,A1 .Location in patent: Paragraph 00256

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
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Code	Phrase
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P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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Code	Phrase
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P321
P322
P330	Rinse mouth.
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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.
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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.
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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
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. 22387-37-7 ] {[proInfo.proName]}

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[ 22387-37-7 ] Synthesis Path-Upstream 1~6

[ 22387-37-7 ] Synthesis Path-Downstream 1~16

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