708-75-8

Basic information

• Product Name: 6-METHYLPTERINE
• Synonyms: 6-METHYLPTERINE;6-methylpterin;4(1H)-Pteridinone,2-amino-6-methyl-(8CI,9CI);2-AAMINO-6-METHYLPTERIDIN-4(1H)-ONE;2-Amino-4-hydroxy-6-methylpteridine;2-Amino-6-methyl-3,4-dihydropteridine-4-one;2-Amino-6-methylpteridin-4(1H)-one;2-Amino-6-methylpteridine-4(3H)-one
• CAS NO: 708-75-8
• Molecular Formula: C₇H₇N₅O
• Molecular Weight: 177.16338
• Product Categories: PIPERIDINE
• Mol File: 708-75-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 432 °C at 760 mmHg
• Flash Point: 215.1 °C
• Appearance: /
• Density: 1.76 g/cm³
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Refractive Index: 1.842
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly, Heated, Sonicated), Aqueous Base (Slightly)
• PKA: pKa 2.5(H2O,t undefined,I=0.1) (Uncertain)
• CAS DataBase Reference: 6-METHYLPTERINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYLPTERINE(708-75-8)
• EPA Substance Registry System: 6-METHYLPTERINE(708-75-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 708-75-8(Hazardous Substances Data)

Usage

Uses

6-Methylpterin is a derivative of Folic Acid (F680300) which is a precursor of coenzymes involved in metabolism of various nucleotides and nucleic acids.

InChI:InChI=1/C7H7N5O/c1-3-2-9-5-4(10-3)6(13)12-7(8)11-5/h2H,1H3,(H3,8,9,11,12,13)

Synthetic route

propylene glycol (57-55-6) + 2,5,6-triaminopyrimidin-4(3H)-one sulfate → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With sodium hydrogensulfite; sodium sulfite In water at 0 - 20℃; for 13h;	80%

2,5,6-triamino-4-hydroxypyrimidine (1004-75-7) + 2-oxopropanal (78-98-8) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
Stage #1: 2,5,6-triamino-4-hydroxypyrimidine With sodium sulfite In water Stage #2: 2-oxopropanal With sodium hydrogensulfite In water at 5 - 20℃;	80%

2,4,5-triamino-6-hydroxypyrimidine sulfate (35011-47-3) + 2-oxopropanal (78-98-8) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With sodium metabisulfite; sodium sulfite In water at 0 - 25℃; for 16.5h;	75%

2-oxopropanal (78-98-8) + 2,5,6-triaminopyrimidin-4(3H)-one dihydrochloride → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
In water at 0 - 5℃; for 0.0172222h; Isay condensation; microwave irradiation;	70%

6-methyl-2-pivaloylamino-4(3H)-pteridinone (142645-50-9) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With perchloric acid at 70 - 80℃; for 0.25h;	62%

7-methoxy-6-methylpterin (113193-95-6) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8) + 2-Amino-8-ethyl-1,9-dihydro-purin-6-one (113193-97-8)

Conditions	Yield
With aluminum-mercury amalgam; ammonia In methanol; water for 10h; Ambient temperature;	A 14% B 42%

dihydroxyacetone (96-26-4) + 2,5,6-triaminopyrimidin-4(3H)-one dihydrochloride → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
for 0.0177778h; Isay condensation; microwave irradiation;	40%

2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + N-acetyl-α-aminopropionaldehyde (73323-67-8) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 120h; Product distribution; various substituted carbonyl compounds, regioselectivity;	30%
With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 120h;	30%

1,1-Dichloroacetone (513-88-2) + 2,5,6-triaminopyrimidin-4(3H)-one dihydrochloride → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
for 0.0208333h; Isay condensation; microwave irradiation;	28%

methanol (67-56-1) + 2,5,6-triamino-3,4-dihydro-4-pyrimidinone (1004-75-7) + 1,1-Dichloroacetone (513-88-2) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
bei pH 1.6;

2,4-diamino-6-methylpteridine (708-74-7) + 1-methyl-4-nitrosobenzene (623-11-0) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
unter Ausschluss von Luft;

2,4-diamino-6-methylpteridine (708-74-7) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With sodium hydroxide; water

(2-amino-4-oxo-3,4-dihydro-pteridin-6-yl)-acetic acid (120568-20-9) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
at 280℃;

1-(2-amino-4-oxo-3,4-dihydro-pteridin-6-ylmethyl)-pyridinium; iodide → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With sodium hydroxide; zinc und anschliessend mit wss.H2O2;

1,1-dibutoxy-2-propanone (19255-82-4) + 2,4,5-triaminopyrimidin-6(1H)-one sulfate monohydrate (35011-47-3) → 7-methylpterin (13040-58-9) + 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With sodium disulfite In water at 80℃; for 6h; Product distribution; further cyclizating agents;

2,4,5,6-tetraaminopyrimidine sulfate (5392-28-9) + 1-(4'-chlorobenzenesulfonyl)-4-methylimidazolin-2-one (79614-36-1) → 7-methylpterin (13040-58-9) + 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With piperidine; potassium hydroxide 1.) water, 20 deg C, 7 d, 2.) heating; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

6-methyldihydropterin hydrochloride (102069-94-3) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8) + 6-Methyl-7,8-dihydropterin (17377-13-8) + (6-R,S)-6-methyl-5,6,7,8-tetrahydropterin dihydrochloride (35695-16-0, 66216-72-6, 67129-01-5, 67129-04-8, 69113-63-9, 74879-09-7, 74923-39-0, 82970-20-5)

Conditions	Yield
With hydrogenchloride pH 3.0; Yields of byproduct given;	A n/a B 35 % Chromat. C n/a
With hydrogenchloride Product distribution; pH 3.0;	A n/a B 35 % Chromat. C n/a

hydroxy-2-propanone (116-09-6) + 2,4,5-triamino-6-hydroxypyrimidine dihydrochloride → 7-methylpterin (13040-58-9) + 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
Yield given. Multistep reaction;

6-Methyl-7,8-dihydropterin (17377-13-8) → 2-amino-6-methylpteridin-4(1H)-one (708-75-8)

Conditions	Yield
With dihydrogen peroxide at 37℃; pH=7.0; Kinetics;
With oxygen In water at 25℃; pH=7.0; Kinetics; Temperature;	Ca. 50 %Chromat.

2-amino-6-methylpteridin-4(1H)-one (708-75-8) → C7H4(2)H5N5O*2Cl(2)H

Conditions	Yield
With sodium dithionite; deuteriated sodium hydroxide In water-d2 at 22℃; for 48h;	87%

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + 2,2-dimethylpropanoic anhydride (1538-75-6) → 6-methyl-2-pivaloylamino-4(3H)-pteridinone (142645-50-9)

Conditions	Yield
	78%
With dmap for 3h; Heating;	40%

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-{[(dimethylamino)methylene]amino}-3,6-dimethylpteridin-4(3H)-one (479414-70-5)

Conditions	Yield
In 1,4-dioxane for 3h; Heating;	74%

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-{[(dimethylamino)methylene]amino}-6-methylpteridin-4(3H)-one (479414-72-7)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 3.5h;	71%

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + acetic anhydride (108-24-7) → N-(6-methyl-4-oxo-1,4-dihydropteridin-2-yl)acetamide (19962-30-2)

Conditions	Yield
With acetic acid at 140℃;	70%

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + benzenesulfonic acid (98-11-3) → 6-methyl-5,6,7,8-tetrahydrobopterin (942-41-6)

Conditions	Yield
Stage #1: bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran; methanol Stage #2: 2-amino-6-methylpteridin-4(1H)-one; benzenesulfonic acid With hydrogen In methanl at 70℃; under 60006 Torr; for 15h; Product distribution / selectivity;	63%

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + 2-Methylpropionic anhydride (97-72-3) + isobutyric Acid (79-31-2) → N-(6-methyl-4-oxo-3,4-dihydropteridin-2-yl)isobutyramide

Conditions	Yield
With dmap at 80℃; for 2h;	62%

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + 2-Methylpropionic anhydride (97-72-3) → N-(6-methyl-4-oxo-3,4-dihydropteridin-2-yl)isobutyramide

Conditions	Yield
With pyridine for 4.5h; Reflux;	57%

2-amino-6-methylpteridin-4(1H)-one (708-75-8) → 6-methyl-1,2,3,4-tetrahydropteridine-2,4-dione (13401-19-9)

Conditions	Yield
With perchloric acid at 110 - 130℃; for 0.75h;	42%
With hydrogenchloride; acetic acid; sodium nitrite

7-methylpterin (13040-58-9) + 2-amino-6-methylpteridin-4(1H)-one (708-75-8) → (2-amino-6-methyl-4-oxo-4,8-dihydro-3H-pteridin-7-yliden)-(2-amino-4-oxo-3,4-dihydro-pteridin-7-yl)-methane

Conditions	Yield
With sulfuric acid unter Zutritt von Luft;

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + 6,7-Dimethylpterin (611-55-2) → (2-amino-6-methyl-4-oxo-3,4-dihydro-pteridin-7-yl)-(2-amino-6-methyl-4-oxo-4,8-dihydro-3H-pteridin-7-ylidene)-methane

2-amino-6-methylpteridin-4(1H)-one (708-75-8) + acrylonitrile (107-13-1) → 7-amino-2-methyl-8,9-dihydro-pyrimido[2,1-b]pteridin-11-one (114205-18-4)

Conditions	Yield
With pyridine

2-amino-6-methylpteridin-4(1H)-one (708-75-8) → 3-amino-6-methyl-pyrazine-2-carboxylic acid (4896-36-0)

Conditions	Yield
With sodium hydroxide

2-amino-6-methylpteridin-4(1H)-one (708-75-8) → 7-methylpterin (13040-58-9)

2-amino-6-methylpteridin-4(1H)-one (708-75-8) → 6-Methyl-7,8-dihydropterin (17377-13-8)

Conditions	Yield
bei der elektrochemischen Reduktion an einer Quecksilber-Kathode;

2-amino-6-methylpteridin-4(1H)-one (708-75-8) → 6-methyl-5,6,7,8-tetrahydrobopterin (942-41-6)

Conditions	Yield
With sodium hydroxide Hydrogenation;
With hydrogen; benzenesulfonic acid; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In methanol at 70℃; under 60006 Torr; for 15h; Product distribution / selectivity;

2-amino-6-methylpteridin-4(1H)-one (708-75-8) → (6R,S)-5-Formyl-6-methyl-5,6,7,8-tetrahydropterin (3116-65-2)

Conditions	Yield
With formic acid; platinum Hydrogenation.und Behandeln des Reaktionsgemisches mit Acetanhydrid;

2-amino-6-methylpteridin-4(1H)-one (708-75-8) → 2-amino-6-dibromomethyl-3H-pteridin-4-one; hydrobromide

Conditions	Yield
With water; hydrogen bromide; bromine

Upstream product

• 708-74-7 2,4-diamino-6-methylpteridine 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 57-55-6 propylene glycol 
• 19255-82-4 1,1-dibutoxy-2-propanone 
• 35011-47-3 2,4,5-triaminopyrimidin-6(1H)-one sulfate monohydrate 
• 102069-94-3 6-methyldihydropterin hydrochloride 
• 113193-95-6 7-methoxy-6-methylpterin 
• 513-88-2 1,1-Dichloroacetone 
• 96-26-4 dihydroxyacetone 
• 7732-18-5 water 
• 127-09-3 sodium acetate 
• 116-09-6 hydroxy-2-propanone 
• 302-01-2 hydrazine 
• 7803-57-8 hydrazine hydrate 

Downstream Products

• 942-41-6 6-methyl-5,6,7,8-tetrahydrobopterin 
• 712-38-9 6-methylisoxanthopterin 
• 142645-52-1 2-(2,2-Dimethyl-propionylamino)-6-methyl-4-oxo-4,6,7,8-tetrahydro-3H-pteridine-5-carboxylic acid benzyl ester 
• 708-74-7 2,4-diamino-6-methylpteridine 
• 142645-50-9 6-methyl-2-pivaloylamino-4(3H)-pteridinone 
• 17377-13-8 6-Methyl-7,8-dihydropterin 
• 13040-58-9 7-methylpterin 
• 4896-36-0 3-Amino-6-methyl-pyrazin-2-carbonsaeure 

Relevant articles and documents

-

-

IMPROVER FOR INFLAMMATORY DISEASE OR ISCHEMIC DISEASE

PROBLEM TO BE SOLVED: To provide a new improver for inflammatory disease or ischemic disease. SOLUTION: The present invention provides an improver for inflammatory disease or acute ischemic disease containing an MAIT cell function inhibitor as an active ingredient. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Reaction between 7,8-dihydropterins and hydrogen peroxide under physiological conditions

In vitiligo, a common skin disorder that produces white patches of depigmentation, 7,8-dihydropterins accumulate in the presence of high concentration of H2O2. In this work, we present a study of the reaction between 7,8-dihydropterins and H2O2. The rate of the reaction, as well as the products formed, strongly depend on the chemical structure of the substituents. Electron-donor groups as substituents are the most reactive derivatives and undergo oxidation of the pterin moiety. The corresponding bimolecular rate constants at 37 °C in neutral aqueous solutions are reported. The biological implications of the results obtained are also discussed.

One-step synthesis of lumazine and xanthine: First co-crystal of lumazine and perchloric acid with a unique monohydrated hydronium ion (H 5O2+) mediated supramolecular assembly of the lumazine dimer

A perchloric acid mediated one-step synthesis of lumazine derivatives from pterins and xanthine from guanine is reported. However, 2-pivaloylamino derivatives of pterins underwent simple hydrolysis of the pivaloylamino group generating free pterin compounds, but the 2-oxo derivatives, that is, the lumazine compounds, were not obtained. A novel supramolecular assembly is constructed by the unique hydrogen bonding of H5O2 + bridging two hydrogen-bonded dimers of lumazine to form the co-crystal 21 with aqueous perchloric acid. In contrast, N2-pivaloyl- 6-bromo-5-deazapterin was simply hydrolysed to form the protonated deazapterin 22, which forms a unique six-membered cyclic hydrogen-bonded structure leading to the generation of a polymeric supramolecular assembly. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.