ChemicalBook > CAS DataBase List > 2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE

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

Product Name: 2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE
CAS No.: 945-24-4
Chemical Name: 2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE
Synonyms: Methotrexate EP Impurity A;AKOS 213-118;Methotrexate-EP-Imp-A;Methotrexate IMpurity A;Pralatrexate Impurity 3;Methotrexate Impurity 1(EP-A);2,4-Diaminopteridine-6-methanol;2,4-DIAMINO-6-PTERIDINEMETHANOL;2,4-diaminopteridine-6-ylmethanol;6-pteridinemethanol, 2,4-diamino-
CBNumber: CB4364405
Molecular Formula: C7H8N6O
Formula Weight: 192.18
MOL File: 945-24-4.mol

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

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)
pka: 12.00±0.10(Predicted)
form: Solid
color: Light Brown to Dark Yellow
InChI: InChI=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)
InChIKey: CYNARAWTVHQHDI-UHFFFAOYSA-N
SMILES: N1=C2C(N=C(CO)C=N2)=C(N)N=C1N
CAS DataBase Reference: 945-24-4(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 22
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 861634
Product name: 2,4-Diamino-6-(hydroxymethyl)pteridine
Purity: 95%
Packaging: 25mg
Price: $77.4
Updated: 2025/07/31

TRC

Product number: P840095
Product name: 2,4-Pteridinediamine-6-methanol
Packaging: 25mg
Price: $65
Updated: 2021/12/16

TRC

Product number: P840095
Product name: 2,4-Pteridinediamine-6-methanol
Packaging: 250mg
Price: $155
Updated: 2021/12/16

ChemScene

Product number: CS-B0318
Product name: (2,4-Diaminopteridin-6-yl)methanol
Packaging: 1g
Price: $104
Updated: 2021/12/16

AK Scientific

Product number: 3136AH
Product name: 2,4-Diamino-6-(hydroxymethyl)pteridine
Packaging: 25g
Price: $370
Updated: 2021/12/16

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2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE Chemical Properties,Usage,Production

Chemical Properties

Orange-Yellow Solid

Uses

2,4-Pteridinediamine-6-methanol (Methotrexate EP Impurity A) is an impurity of Methotrexate. A useful reagent for the development of selective antiparasitic compounds.

Synthesis

96-26-4

5392-28-9

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

2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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