73978-41-3

Basic information

• Product Name: (2,4-DIAMINOPTERIDIN-6-YL)METHANOL HYDROCHLORIDE HYDRATE
• Synonyms: (2,4-DIAMINOPTERIDIN-6-YL)METHANOL HYDROCHLORIDE HYDRATE;2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE HYDROCHLORIDE HYDRATE;2,4-Diamino-8-(hydroxymethyl)pteridinehydrochloride;2,4-Diamino-6-(Hydroxymethyl)pteridine HCl;2,4-diamino-6-(hydroxymethyl)pteridine hydrocloride;(2,4-DIAMINOPTERIDIN-6-YL)METHANOL HYDROCHLORIDE H;2,4-DiaMinopyriMido[4,5-b]pyrazine-6-Methanol Monohydrochloride;4-DiaMino-6-pteridineMethanol Hydrochloride
• CAS NO: 73978-41-3
• Molecular Formula: C₇H₈N₆O*ClH
• Molecular Weight: 228.64
• EINECS: 1308068-626-2
• Product Categories: Heterocycles series;Hydroxymethyl's;Fused Ring Systems;Building Blocks;Heterocyclic Building Blocks;Quinazolines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 73978-41-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 220 °C(lit.)
• Boiling Point: 560.2 °C at 760 mmHg
• Flash Point: 292.6 °C
• Appearance: /
• Vapor Pressure: 4.47E-17mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: 10g/L at 20℃
• CAS DataBase Reference: (2,4-DIAMINOPTERIDIN-6-YL)METHANOL HYDROCHLORIDE HYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (2,4-DIAMINOPTERIDIN-6-YL)METHANOL HYDROCHLORIDE HYDRATE(73978-41-3)
• EPA Substance Registry System: (2,4-DIAMINOPTERIDIN-6-YL)METHANOL HYDROCHLORIDE HYDRATE(73978-41-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 73978-41-3(Hazardous Substances Data)

Usage

Description

(2,4-Diamino-pteridin-6-yl)methanol hydrochloride hydrate is an organic compound that serves as an intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is a white to light yellow crystalline powder with unique chemical properties that make it a valuable component in the development of drugs and other chemical products.

Uses

Used in Pharmaceutical Industry:
(2,4-Diamino-pteridin-6-yl)methanol hydrochloride hydrate is used as a methotrexate intermediate for the synthesis of methotrexate, a widely used anti-cancer and anti-inflammatory drug. It plays a crucial role in the production of this medication, contributing to its effectiveness in treating various conditions.
Used in Chemical Synthesis:
(2,4-Diamino-6-(hydroxymethyl)pteridine hydrochloride) may be used in the synthesis of 6-bromomethyl-pteridine-2,4-diamine, a compound with potential applications in various chemical and pharmaceutical processes. This versatile intermediate allows for the creation of new compounds with diverse uses.

InChI:InChI=1/C7H8N6O.ClH.H2O/c8-5-4-6(13-7(9)12-5)10-1-3(2-14)11-4;;/h1,14H,2H2,(H4,8,9,10,12,13);1H;1H2

Synthetic route

2,4,5,6-tetraaminopyrimidine (1004-74-6) + dihydroxyacetone (96-26-4) → 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride (73978-41-3)

Conditions	Yield
With oxygen; DL-cysteine hydrochloride; ammonium chloride In water for 36h;	70%

dihydroxyacetone (96-26-4) + 2,4,5,6-tetraaminopyrimidine sulfate (5392-28-9) → 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride (73978-41-3)

Conditions	Yield
With ammonium hydroxide; l-cysteine hydrochloride; oxygen; ammonium chloride; barium(II) chloride 1.) H2O, 90 deg C, 15 min, 2.) H2O, RT, 45 h; Yield given. Multistep reaction;

1,3-dihydroxyacetone dimer (62147-49-3) + barium chloride dihydrate + 2,4,5,6-tetraminopyrimidine sulfate monohydrate + DL-cysteine hydrochloride (10318-18-0) → 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride (73978-41-3)

Conditions	Yield
With ammonium chloride In water	17.2 g (45%)

Upstream product

• 1004-74-6 2,4,5,6-tetraaminopyrimidine 
• 96-26-4 dihydroxyacetone 
• 5392-28-9 2,4,5,6-tetraaminopyrimidine sulfate 
• 62147-49-3 1,3-dihydroxyacetone dimer 
• 10318-18-0 DL-cysteine hydrochloride 

Downstream Products

• 712-29-8 6-(hydroxymethyl)pterin 
• 945-24-4 2,4-diamino-6-(hydroxymethyl)pteridine 
• 59368-16-0 6-bromomethyl-pteridine-2,4-diamine 
• 52853-40-4 6-bromomethyl-2,4-diaminopteridine hydrobromide 
• 19741-14-1 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid 
• 79640-70-3 (S)-5-(tert-butoxy)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid 

Relevant articles and documents

Pteridine derivatives and method of treating leukemia employing same

2,4-Diaminopteridine derivatives and the pharmaceutically acceptable salts thereof having potent anticancer activity are disclosed. The derivatives possess the structural formula: STR1 wherein Y is NH2, OH or SH, R is STR2 and X is STR3 in which R' is H or CH3 or STR4 in which R and R' are as previously defined, provided when Y is NH2, R' must be CH3 and when Y is OH, R' must be OH.

Pteridines, LXIX. Synthesis and Reactivity of 2,4-Diamino-6-(hydroxymethyl)pteridine

Condensation of 2,4,5,6-tetraaminopyridine (2) with 1,3-dihydroxyacetone in the presence of gaseous oxygen, rather than air, resulted in 2,4-diamino-6-(hydroxymethyl)pteridine (3) virtually uncontaminated with 2,4-diamino-6-methylpteridine (4).Acetylation of 3 led to 6-acetoxymethyl-2,4-bis(acetylamino)pteridine (5) which turned out to be very labile forming various di- and monoacetyl derivatives (6, 7, 9, 10) on mild hydrolytic conditions.Their structures are proven by physical-chemical means.Silylation of 3 to the tris(trimethylsilyl) derivative 11 followed by treatment with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (12) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (15), respectively, in the presence of boron trifluoride,led to selective formation of the corresponding acylated 2,4-diamino-6-pteridinyl O-glycosides 13 and 15, respectively.Deacylations of these afforded the free O-glycosides 14 and 17 which have been characterized by UV- and NMR spectra as well as pKa measurements.