2,4-Diaminopyrimidine Chemical Properties

Melting point:

143-147 °C (lit.)

Boiling point:

401.7±37.0 °C(Predicted)

Density 

1.368±0.06 g/cm3(Predicted)

refractive index 

1.46-1.466

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

pka

7.08±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

Water Solubility 

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 DataBase Reference

156-81-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29335990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2,4-Diaminopyrimidine Usage And Synthesis

Chemical Properties

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.

Synthesis

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).

References

[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

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