4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro- (9CI) Chemical Properties

Melting point:

>300 °C(Solv: water (7732-18-5))

Density 

1.87±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

pka

10.85±0.20(Predicted)

form 

Solid

color 

Beige

4H-Pyrrolo[3,2-d]pyrimidin-4-one, 2-amino-1,5-dihydro- (9CI) Usage And Synthesis

Description

9-Deazaguanine is an analog of guanine that acts as an inhibitor of purine nucleoside phosphorylase (PNP; K_d = 160 nM). Inhibitors of PNP are used to control T cell proliferation, particularly in T cell cancers, autoimmune diseases, and tissue transplant rejection.

Chemical Properties

Beige Solid

Uses

A nucleoside analog as potent inhibitor of purine nucleoside phosphorylase.

Synthesis

General procedure for the synthesis of 2-amino-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one from the compound (CAS: 224946-82-1): 2-amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (10 g, 0.04 mol) was dissolved in methanol (334 mL), 10% Pd/C (2 g) and formic acid ammonium (13.2 g, 0.21 mol). The reaction mixture was heated at 75°C for 4 hours. After completion of the reaction, the reaction mixture was cooled and filtered through a diatomaceous earth pad with hot 1:1 DMF/MeOH solvent mixture. The filtrate was concentrated under vacuum to afford the off-white solid product 2-amino-3-benzyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (6.2 g, 99% yield).

References

[1] Patent: WO2006/122003, 2006, A2. Location in patent: Page/Page column 32; 36

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