[ CAS No. 15981-91-6 ] {[proInfo.proName]}

Name: 15981-91-6|2-Amino-5-methylpyrimidin-4(3H)-one|95%
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3d Animation Molecule Structure of 15981-91-6

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Quality Control of [ 15981-91-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 15981-91-6 ]

SDS Specification

Alternatived Products of [ 15981-91-6 ]

Product Details of [ 15981-91-6 ]

CAS No. :	15981-91-6	MDL No. :	MFCD09754456
Formula :	C₅H₇N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YKUFMYSNUQLIQS-UHFFFAOYSA-N
M.W :	125.13	Pubchem ID :	85221
Synonyms :

Calculated chemistry of [ 15981-91-6 ] Expand+

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 :	2.0
Molar Refractivity :	34.23
TPSA :	71.77 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) :	-7.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.58
Log Po/w (XLOGP3) :	-0.92
Log Po/w (WLOGP) :	-0.33
Log Po/w (MLOGP) :	-0.44
Log Po/w (SILICOS-IT) :	0.81
Consensus Log Po/w :	-0.06

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.53
Solubility :	37.0 mg/ml ; 0.295 mol/l
Class :	Very soluble
Log S (Ali) :	-0.1
Solubility :	98.6 mg/ml ; 0.788 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.54
Solubility :	3.57 mg/ml ; 0.0285 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 15981-91-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 15981-91-6 ]

* 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 [ 15981-91-6 ]
Downstream synthetic route of [ 15981-91-6 ]

[ 15981-91-6 ] Synthesis Path-Upstream 1~1

1
[ 15981-91-6 ]
[ 20090-58-8 ]

Yield	Reaction Conditions	Operation in experiment
29%	Stage #1: for 0.75 h; Reflux Stage #2: With ammonia In water at 10℃;	Step b: 4-Chloro-2-amino-5-methylpyrimidineA mixture of 5-methylisocytosine (3 g, 24.0 mmol) and POCl₃(20 mL) was refluxed for 45 minutes. Excess of POCl₃was removed under reduced pressure and the residue was poured over ice. The resulting mixture was made basic with ammonia at 10° C. The precipitate was filtrated and crystallized from ethanol to give 4-chloro-2-amino-5-methylpyrimidine (1 g 29.0percent yield). ¹H NMR (400 MHz, DMSO): δ 8.11 (s, 1 H), 6.81 (br s, 2 H), 2.04 (s, 3 H).

Reference： [1] Patent: US2009/221597, 2009, A1, . Location in patent: Page/Page column 41
[2] Journal of the Chemical Society, 1947, p. 41,45

[ 15981-91-6 ] Synthesis Path-Downstream 1~17

1
[ 608-41-3 ]
[ 50-01-1 ]
[ 15981-91-6 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 912

2
[ 15981-91-6 ]
[ 20090-58-8 ]

Yield	Reaction Conditions	Operation in experiment
29%		Step b: 4-Chloro-2-amino-5-methylpyrimidineA mixture of 5-methylisocytosine (3 g, 24.0 mmol) and POCl3 (20 mL) was refluxed for 45 minutes. Excess of POCl3 was removed under reduced pressure and the residue was poured over ice. The resulting mixture was made basic with ammonia at 10 C. The precipitate was filtrated and crystallized from ethanol to give 4-chloro-2-amino-5-methylpyrimidine (1 g 29.0% yield). 1H NMR (400 MHz, DMSO): delta 8.11 (s, 1 H), 6.81 (br s, 2 H), 2.04 (s, 3 H).

Reference： [1]Patent: US2009/221597,2009,A1 .Location in patent: Page/Page column 41
[2]Journal of the Chemical Society,1947,p. 41,45

3
[ 4401-71-2 ]
[ 113-00-8 ]
[ 15981-91-6 ]

Reference： [1]Heterocycles,1984,vol. 21,p. 289 - 307

4
[ 27772-62-9 ]
[ 50-01-1 ]
[ 15981-91-6 ]
[ 134277-54-6 ]
[ 134277-56-8 ]
[ 134277-55-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 231 - 236
[2]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 231 - 236

5
[ 15981-91-6 ]
[ 65-71-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 231 - 236

6
[ 19449-30-0 ]
[ 15981-91-6 ]
2-[(N,N-di(n-butyl)amino)methylidene]amino-5-methyl-4(3H)-pyrimidinone [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 9481 - 9500

7
[ 15981-91-6 ]
[ 4637-24-5 ]
2-[(N,N-dimethylamino)methylidene]amino-5-methyl-4(3H)-pyrimidinone [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 9481 - 9500

8
[ 19316-88-2 ]
[ 15981-91-6 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 9481 - 9500

9
[ 190274-88-5 ]
[ 15981-91-6 ]
dmf²m⁵iCyt [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 9481 - 9500

12
β-guanidino-α-methyl-acrylic acid [ No CAS ]
[ 15981-91-6 ]

Reference： [1]American Chemical Journal,1904,vol. 32,p. 144

13
[ 50-01-1 ]
sodium-compound of 2-methyl-3-oxo-propionic acid ethyl ester [ No CAS ]
[ 15981-91-6 ]

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

14
[ 5815-08-7 ]
[ 15981-91-6 ]
2-[(dimethylamino)methyleneamino]-5-methylpyrimidin-4-one [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 1375 - 1387

15
[ 15981-91-6 ]
<i>N</i>⁴-(2-diethylamino-ethyl)-5-methyl-pyrimidine-2,4-diyldiamine [ No CAS ]

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

16
[ 15981-91-6 ]
<i>N</i>⁴-(3-diethylamino-propyl)-5-methyl-pyrimidine-2,4-diyldiamine [ No CAS ]

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

17
[ 107-31-3 ]
[ 50-01-1 ]
[ 105-37-3 ]
[ 15981-91-6 ]

Yield	Reaction Conditions	Operation in experiment
58.4%		Preparation of 3-(2-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-5-methylpyrimidin-4-yl)benzoic acid Step a: 5-MethylisocytosineFreshly prepared sodium methoxide (10.8 g, 200 mmol) was suspended in a solution of ethyl propionate (15.3 g, 150 mmol) in DMF (20 mL) at room temperature. Methyl formate (6.0 g, 100 mmol) was added over a period of 1 hour. After stirring for 30 minutes, a solution of guanidine hydrochloride (9.6 g g, 100 mmol) in MeOH (35 mL) was added rapidly and the reaction mixture was refluxed for 12 hours. After cooling to 30 C. and adjusting the pH to 6.0 with concentrated hydrochloric acid, the slurry was kept at 5 C. for 30 minutes. The solid was collected, washed with methanol, crystallized from water and dried in vacuo to give 5-methylisocytosine (7.3 g, 58.4% yield). 1H NMR (300 MHz, DMSO): δ10.83 (br s, 2 H), 7.38 (s, 1 H), 6.26 (br s, 2 H), 1.72 (s, 3 H).

Reference： [1]Patent: US2009/221597,2009,A1 .Location in patent: Page/Page column 40; 41

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Isomers

Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Acyl Group Substitution • Amide Hydrolysis • Amide Hydrolysis • 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 • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complex Metal Hydride Reductions • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Enamine Formation • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitrosation of Amines • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Amines • Preparation of LDA • Reactions of Amines • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Synthesis of 2-Amino Nitriles • Ugi Reaction

Historical Records

Related Functional Groups of
[ 15981-91-6 ]

Amides

[ 28224-63-7 ]

2-Amino-5-ethylpyrimidin-4(3H)-one

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Amines

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Related Parent Nucleus of
[ 15981-91-6 ]

Pyrimidines

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P233	Keep container tightly closed.
P234	Keep only in original container.
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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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.
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.
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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.
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P370 + P378	In case of fire:
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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
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H221	Flammable gas
H222	Extremely flammable aerosol
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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
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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
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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
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H370	Causes damage to organs
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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. 15981-91-6 ] {[proInfo.proName]}

Quality Control of [ 15981-91-6 ]

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Product Details of [ 15981-91-6 ]

Calculated chemistry of [ 15981-91-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 15981-91-6 ]

Application In Synthesis of [ 15981-91-6 ]

[ 15981-91-6 ] Synthesis Path-Upstream 1~1

[ 15981-91-6 ] Synthesis Path-Downstream 1~17

Technical Information

Related Functional Groups of [ 15981-91-6 ]

Amides

Amines

Related Parent Nucleus of [ 15981-91-6 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 15981-91-6 ]

Related Parent Nucleus of
[ 15981-91-6 ]