1431-40-9|2-(Methylthio)pyrimidine-4,5,6-triamine| Ambeed

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Quality Control of [ 1431-40-9 ] Purity: 95% SDS Specification

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Product Details of [ 1431-40-9 ]

CAS No. :	1431-40-9
Formula :	C₅H₉N₅S
M.W :	171.22
SMILES Code :	NC1=NC(SC)=NC(N)=C1N
MDL No. :	MFCD00023239
InChI Key :	CTHYWCCCVXWRCA-UHFFFAOYSA-N
Pubchem ID :	229266

Safety of [ 1431-40-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1431-40-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	3.0
Molar Refractivity	46.97
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	129.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.94
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.33
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.03
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.78
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.63
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.17

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.03
Solubility	15.9 mg/ml ; 0.093 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.92
Solubility	2.06 mg/ml ; 0.012 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.07
Solubility	14.6 mg/ml ; 0.0853 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.58 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.23

Application In Synthesis of [ 1431-40-9 ]

* 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.

Downstream synthetic route of [ 1431-40-9 ]

[ 1431-40-9 ] Synthesis Path-Downstream 1~34

1
[ 64-18-6 ]
[ 1431-40-9 ]
N-(4,6-diamino-2-methylsulfanyl-pyrimidin-5-yl)-formamide [ No CAS ]

References: [1]Journal of the Chemical Society,1945,p. 556,561.

2
[ 4230-33-5 ]
[ 1431-40-9 ]
[ 5221-17-0 ]
[ 94543-82-5 ]

References: [1]Comptes rendus hebdomadaires des seances de l'Academie des sciences,1956,vol. 243,p. 2172 - 2174.

3
[ 1431-40-9 ]
[ 5221-17-0 ]
[ 150-13-0 ]
[ 93898-79-4 ]

References: [1]Comptes rendus hebdomadaires des seances de l'Academie des sciences,1956,vol. 243,p. 2172 - 2174.

4
[ 1431-40-9 ]
[ 69316-68-3 ]
[ 98197-66-1 ]

References: [1]Journal of the Chemical Society,1943,p. 383,384.
Journal of the Chemical Society,1944,p. 318,321.

5
[ 1431-40-9 ]
[ 431-03-8 ]
[ 19152-98-8 ]

References: [1]Journal of the American Chemical Society,1952,vol. 74,p. 1644,1646.

6
[ 1431-40-9 ]
[ 95-92-1 ]
4-amino-2-methylsulfanyl-5,8-dihydro-pteridine-6,7-dione [ No CAS ]

References: [1]Journal of the Chemical Society,1951,p. 3,6.

7
[ 1431-40-9 ]
[ 134-81-6 ]
[ 15263-43-1 ]

References: [1]Journal of the American Chemical Society,1952,vol. 74,p. 1644,1646.

8
[ 1431-40-9 ]
5-chloro-[1,2,5]thiadiazolo[3,4-d]pyrimidin-7-ylamine [ No CAS ]

References: [1]Journal of Organic Chemistry,1951,vol. 16,p. 207,208, 211, 213.
[2]Journal of Organic Chemistry,1951,vol. 16,p. 207,208, 211, 213.

9
[ 1431-40-9 ]
[ 87866-19-1 ]

References: [1]Journal of the Chemical Society,1958,p. 1593,1597.

10
[ 52222-43-2 ]
[ 1431-40-9 ]

References: [1]Journal of the American Chemical Society,1952,vol. 74,p. 1644,1646.
[2]Journal of the Chemical Society,1943,p. 383,384.
Journal of the Chemical Society,1944,p. 318,321.
[3]Helvetica Chimica Acta,1990,vol. 73,p. 808 - 826.
[4]Journal of Medicinal Chemistry,1999,vol. 42,p. 4108 - 4121.
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 10080 - 10100.

11
[ 1431-40-9 ]
[ 5336-08-3 ]
[ 102879-86-7 ]

References: [1]Journal of the Chemical Society,1958,p. 4069,4072.

12
[ 1431-40-9 ]
[ 90-80-2 ]
[ 1195634-63-9 ]

References: [1]Journal of the Chemical Society,1958,p. 4069,4072.

13
[ 1431-40-9 ]
[ 6306-87-2 ]

References: [1]Journal of Organic Chemistry,1962,vol. 27,p. 2154 - 2160.

14
[ 1431-40-9 ]
[ 28767-74-0 ]
[ 130790-19-1 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 808 - 826.

15
[ 1431-40-9 ]
[ 622-12-8 ]
[ 130695-40-8 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 808 - 826.

16
[ 1431-40-9 ]
[ 622-12-8 ]
[ 130592-61-9 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 808 - 826.

17
[ 1431-40-9 ]
[ 90687-17-5 ]

References: [1]Pharmaceutical Chemistry Journal,1984,vol. 18,p. 189 - 191.
Khimiko-Farmatsevticheskii Zhurnal,1984,vol. 18,p. 325 - 327.

19
[ 56-23-5 ]
[ 7791-25-5 ]
[ 1431-40-9 ]
5-chloro-[1,2,5]thiadiazolo[3,4-d]pyrimidin-7-ylamine [ No CAS ]

References: [1]Journal of Organic Chemistry,1962,vol. 27,p. 2154 - 2160.

20
[ 56-23-5 ]
[ 1431-40-9 ]
[ 7782-50-5 ]
5-chloro-[1,2,5]thiadiazolo[3,4-d]pyrimidin-7-ylamine [ No CAS ]

References: [1]Journal of Organic Chemistry,1962,vol. 27,p. 2154 - 2160.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 3 4,5,6-Triamino-2-(methylthio)pyrimidine STR13 Sodium hydrosulfite (sodium dithionite, 78.3 g., 0.45 mole) is added in one portion to a stirred suspension of 4,6-diamino-2-(methylthio)-5-nitrosopyrimidine (27.8 g., 0.15 mole) in 300 ml. 1 N sodium hydroxide. Within a 15-20 minute period, the temperature of the mixture increases to 60 with concommitant foaming. The mixture is stirred for a 16 hr. period, insolubles collected and washed well with water, air-dried, and crystallized from acetonitrile to yield 19.73 g. (76.8%) of 4,5,6-triamino-2-(methylthio)pyrimidine as yellow crystals, m.p. 180-182.
		The resulting solution was warmed to a temperature ranging from 60 to 65C and thereto was added Na2S2O4 until color of the solution became disappeared. The resultant clear solution was adjusted to pH 9 and cooled to produce precipitates, which were filtered and dried to obtain 98.4g of the title compound. m.p.: 208C NMR(delta, DMSO-d6): 5.68(s, 4H), 3.58(s, 2H), 2.31(s, 3H)
		Preparation Example 21 : Synthesis of 1,4,5,6-tetraamino pyrimidine-2-thione To a solution of 17.1g of 4,5,6-triamino-2-methylthio pyrimidine, which was obtained in Preparation Example 1 above, dissolved in 100 ml of dichloromethane was added dropwise a solution of 43g of hydroxylamine-0-mesitylene sulfonate dissolved in 50 ml of dichloromethane at 0C.

22
[ 1431-40-9 ]
[ 130695-41-9 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 808 - 826.

23
[ 1431-40-9 ]
[ 130592-62-0 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 808 - 826.

24
[ 1005-39-6 ]
[ 1431-40-9 ]

References: [1]Journal of the Chemical Society,1943,p. 383,384.
Journal of the Chemical Society,1944,p. 318,321.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 10080 - 10100.

25
[ 1431-40-9 ]
[ 1198-83-0 ]

References: [1]Journal of the Chemical Society,1943,p. 383,384.
Journal of the Chemical Society,1944,p. 318,321.

26
[ 213124-94-8 ]
[ 1431-40-9 ]
[ 213248-30-7 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2880 - 2898.

27
[ 73568-25-9 ]
[ 1431-40-9 ]
[ 1214720-43-0 ]

References: [1]European Journal of Organic Chemistry,2010,p. 317 - 325.

28
[ 1431-40-9 ]
[ 501676-50-2 ]
[ 1402415-38-6 ]

References: [1]Archiv der Pharmazie,2012,vol. 345,p. 739 - 744.

29
[ 1431-40-9 ]
[ 111038-89-2 ]
[ 1402415-39-7 ]

References: [1]Archiv der Pharmazie,2012,vol. 345,p. 739 - 744.

30
[ 1431-40-9 ]
[ 849045-70-1 ]
[ 1402415-43-3 ]

References: [1]Archiv der Pharmazie,2012,vol. 345,p. 739 - 744.

31
[ 1431-40-9 ]
[ 110334-09-3 ]
[ 1402415-41-1 ]

References: [1]Archiv der Pharmazie,2012,vol. 345,p. 739 - 744.

32
[ 1005-38-5 ]
[ 1431-40-9 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10080 - 10100.

33
[ 1431-40-9 ]
2-(6-amino-2-(methylthio)-9H-purin-8-ylthio)-N-(3,4-dimethoxyphenyl)acetamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10080 - 10100.

34
[ 75-15-0 ]
[ 1431-40-9 ]
6-amino-2-(methylthio)-7H-purine-8(9H)-thione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10080 - 10100.

Historical Records

Technical Information

• Hydride Reductions • Nucleophilicity of Sulfur Compounds • Oxidation States of Sulfur Compounds

Related Functional Groups of
[ 1431-40-9 ]

Sulfides

A143923 [73000-30-3]

2-(Ethylthio)pyrimidine-4,5,6-triamine

Similarity: 0.92

A183548 [1005-39-6]

2-(Methylthio)pyrimidine-4,6-diamine

Similarity: 0.84

A122372 [2183-66-6]

2-(Methylthio)pyrimidin-4-amine

Similarity: 0.82

Related Parent Nucleus of
[ 1431-40-9 ]

Pyrimidines

A143923 [73000-30-3]

2-(Ethylthio)pyrimidine-4,5,6-triamine

Similarity: 0.92

A143923 [73000-30-3]

2-(Ethylthio)pyrimidine-4,5,6-triamine

Similarity: 0.92

A183548 [1005-39-6]

2-(Methylthio)pyrimidine-4,6-diamine

Similarity: 0.84

A122372 [2183-66-6]

2-(Methylthio)pyrimidin-4-amine

Similarity: 0.82

Precautionary Statements-General
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P102	Keep out of reach of children.
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Prevention
Code	Phrase
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Response
Code	Phrase
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P320
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P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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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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Storage
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P401
P402	Store in a dry place.
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P411
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P413
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P402 + P404	Store in a dry place. Store in a closed container.
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Physical hazards
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H200	Unstable explosive
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H202	Explosive; severe projection hazard
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H242	Heating may cause a fire
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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
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

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CAS No.: 1431-40-9

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