Pyrimidin-2,4-diyldiamin

Bezeichnung:Pyrimidin-2,4-diyldiamin

CAS-Nr156-81-0

Englisch Name:2,4-Diaminopyrimidine

CBNumberCB8763402

SummenformelC4H6N4

Molgewicht110.12

MOL-Datei156-81-0.mol

Synonyma

Pyrimidin-2,4-diyldiamin

Pyrimidin-2,4-diyldiamin physikalisch-chemischer Eigenschaften

Schmelzpunkt	143-147 °C (lit.)
Siedepunkt	401.7±37.0 °C(Predicted)
Dichte	1.368±0.06 g/cm3(Predicted)
Brechungsindex	1.46-1.466
storage temp.	Keep in dark place,Sealed in dry,2-8°C
Aggregatzustand	powder to crystal
pka	7.08±0.10(Predicted)
Farbe	White to Almost white
Wasserlöslichkeit	840 g/L (25 ºC)
InChI	InChI=1S/C4H6N4/c5-3-1-2-7-4(6)8-3/h1-2H,(H4,5,6,7,8)
InChIKey	YAAWASYJIRZXSZ-UHFFFAOYSA-N
SMILES	C1(N)=NC=CC(N)=N1
CAS Datenbank	156-81-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39
WGK Germany	3
HS Code	29335990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

2,4-Diaminopyrimidine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
light orange crystalline powder
Definition
ChEBI: Pyrimidine-2,4-diamine is an aminopyrimidine in which a pyrimidine nucleus is substituted with amino groups at C-2 and C-4.
Synthese

1004-01-9

73183-34-3

156-81-0

944401-61-0

Synthesis of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2,4-diamine: To a dry 1L flask was added 5-bromopyrimidine-2,4-diamine (30.0 g, 158.7 mmol), potassium acetate (45.8 g, 466.7 mmol), pinacol bis(boronic acid) ester (51.16 g, 202.2 mmol) and dioxane (500 mL). After bubbling argon through the solution for 15 minutes, 1,1'-bis(diphenylphosphino)ferrocene palladium(II) chloride (2.53 g, 3.11 mmol) was added. The reaction mixture was refluxed in an oil bath at 115 °C for 16 h under argon protection. After completion of the reaction, it was cooled to room temperature, filtered to remove solid inorganic material and washed with ethyl acetate (1 L). The organic filtrate was concentrated under vacuum and dichloromethane (1 L) was added to the resulting solid. After sonication, the solid was collected by filtration and this solid was the debromination product 2,4-diaminopyrimidine. The filtrate containing the target borate was concentrated in vacuo and ether (100 mL) was added to the residue. After sonication, the filtrate was filtered and washed with additional ether (50 mL), and the resulting solid was dried under high vacuum to afford the target product 2,4-diaminopyrimidine-5-boronic acid pinacol ester (10.13 g, 27% yield). The substance was analyzed by 1H NMR as a 4:1 mixture of 2,4-diaminopyrimidine-5-boronic acid pinacol ester and 2,4-diaminopyrimidine by-product. The mixture could be used in the subsequent Suzuki reaction without further purification.LCMS (m/z): 155 (MH+ of boronic acid, derived from hydrolysis of the in situ product on LC); 1H NMR (CDCl3 + CD3OD): δ8.16 (s, 1H), 1.34 (s, 12H).
Einzelnachweise
[1] Patent: WO2008/98058, 2008, A1. Location in patent: Page/Page column 64-65
[2] Patent: WO2007/84786, 2007, A1. Location in patent: Page/Page column 98
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779
[4] Patent: WO2012/109423, 2012, A1. Location in patent: Page/Page column 23

2,4-Diaminopyrimidine Upstream-Materialien And Downstream Produkte

Pyrimidin-2,4-diyldiamin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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