2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE

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CAS:945-24-4
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Products Intro: Product Name:(2,4-DIAMINOPTERIDIN-6-YL)METHANOL
CAS:945-24-4
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2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE manufacturers

2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE Basic information
Product Name:2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE
Synonyms:AKOS 213-118;(2,4-DIAMINO-PTERIDIN-6-YL)-METHANOL;(2,4-DIAMINO-6-PTERIDINYL)METHANOL;2,4-DIAMINO-6-PTERIDINEMETHANOL;2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE;2,4-diaminopteridine-6-ylmethanol;2,4-Diamino-6-hydroxymethylpteridine hydrochloride or HBR;2,4-DIAMINO-6-HYDROXYMETHYLPTERIDINE, 95 %
CAS:945-24-4
MF:C7H8N6O
MW:192.18
EINECS:213-412-2
Product Categories:Benzhydrols, Benzyl & Special Alcohols;Heterocycles;Aromatics Compounds;Aromatics;Bases & Related Reagents;Inhibitors;Nucleotides
Mol File:945-24-4.mol
2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE Structure
2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE Chemical Properties
Melting point 333-334 °C (decomp)
Boiling point 560.2±60.0 °C(Predicted)
density 1.673±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility DMSO (Slightly), Methanol (Slightly, Heated)
form Solid
pka12.00±0.10(Predicted)
color Light Brown to Dark Yellow
InChIInChI=1S/C7H8N6O/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)
InChIKeyCYNARAWTVHQHDI-UHFFFAOYSA-N
SMILESN1=C2C(N=C(CO)C=N2)=C(N)N=C1N
CAS DataBase Reference945-24-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22
WGK Germany 3
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
MSDS Information
ProviderLanguage
SigmaAldrich English
2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE Usage And Synthesis
Chemical PropertiesOrange-Yellow Solid
Uses2,4-Pteridinediamine-6-methanol (Methotrexate EP Impurity A) is an impurity of Methotrexate. A useful reagent for the development of selective antiparasitic compounds.
Synthesis
1,3-Dihydroxyacetone

96-26-4

Pyrimidinetetramine sulfate

5392-28-9

2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE

945-24-4

1. Barium chloride (7.32 g, 30 mmol) was added rapidly to an aqueous suspension of tetraaminopyrimidine sulfate (7.14 g, 30 mmol). The reaction mixture was heated at 100 °C for 10 min and then cooled to room temperature. The resulting barium sulfate solid was removed by filtration. 2. The above filtrate was transferred to a 1 L three-necked round-bottomed flask fitted with a mechanical stirrer pre-filled with 450 mL of an aqueous 4 M sodium acetate solution containing dihydroxyacetone (8 g, 90 mmol) and cysteine hydrochloride monohydrate (3.63 g, 30 mmol). The reaction mixture was stirred at room temperature, open to air for 24 hours. 3. Upon completion of the reaction, the precipitated yellow solid was collected by filtration, washed sequentially with water and ethanol, and subsequently dried in a heated vacuum oven overnight to afford 3.4 g (66% yield) of the crude product 2,4-diamino-6-hydroxymethylpteridine. 4. Purification of the crude product: the yellow solid was dissolved in 10% acetic acid and a few drops of concentrated hydrochloric acid were added. The solution was heated to 75°C, treated with the addition of activated carbon and subsequently thermally filtered. 5. Neutralize the filtrate with ammonia to neutral and precipitate a bright yellow solid. The solid was collected by filtration, washed sequentially with water, water-ethanol mixture and ethanol, and finally dried overnight in a heated vacuum oven to give 2.8 g (54% yield) of purified 2,4-diamino-6-hydroxymethylpteridine.

References[1] Patent: WO2010/110907, 2010, A1. Location in patent: Page/Page column 48-49
Tag:2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE(945-24-4) Related Product Information
D(-)-AMETHOPTERIN Methotrexate Related Compound E (50 mg) (4-{[(2,4-Diaminopteridin-6-yl)methyl](methyl)amino}benzoic acid, hemihydrochloride) N-(4-(METHYLAMINO)BENZOYL)-L-GLUTAMIC ACID Methotrexate EP Impurity G Aminopterin 6-(Bromomethyl)-2,4-pteridinediamine hydrobromide L-Glutamic acid, N-[4-[[ (2-amino-1, 4-dihydro-4-oxo-6-pteridinyl)meth yl]methylamino]benzoyl]- Methotrexate 4-[Methyl[(2-amino-4-hydroxypteridine)-6-ylmethyl]amino]benzoic acid 4-(HYDROXYMETHYL)BENZONITRILE 2,4-DIAMINO-6-(HYDROXYMETHYL)-PTERIDINE HYDROBROMIDE 2,4-DIAMINO-6-HYDROXYMETHYL PTERIDINE HYDROBROMID 2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE HYDROCHLORIDE HYDRATE,2,4-Diamino-6-(Hydroxymethyl)pteridine HCl,2,4-diamino-6-(hydroxymethyl)pteridine hydrocloride 2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE HYDROCHLORIDE

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