2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine

2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine Property

Melting point:

>230°C (dec.)

Density 

1.87±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Soluble in N,N-Dimethylformamide, Dimethyl sulfoxide.

form 

crystalline

pka

10.83±0.20(Predicted)

color 

tan

CAS DataBase Reference

7355-55-7(CAS DataBase Reference)

Safety

Risk Statements 

36/37/38

Safety Statements 

26-37-60

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine Chemical Properties,Usage,Production

Chemical Properties

Pink solid

Uses

Ethidium bromide efficiently intercalates into synthetic duplex DNAs with 7-deazaguanine in place of guanine, but shows none of the fluorescence enhancement usually observed upon intercalation. 7-Deazaadenine-duplexes show about 70% of the expected fluorescence enhancement.

Definition

ChEBI: DG is 7-deazaguanine

Synthesis

To a suspension of bromoacetaldehyde diethyl acetal (10.4 mL, 68.98 mmol) in water (35 mL) was slowly added concentrated hydrochloric acid (1.5 mL). The reaction mixture was stirred at 90 °C for 30 min. Upon completion of the reaction, the solution was cooled to room temperature, followed by the addition of sodium acetate (6.8 g, 82.75 mmol). This mixed solution was slowly added to a suspension in water (75 mL) containing 2,4-diamino-6-hydroxypyrimidine (10.0 g, 79.29 mmol) and sodium acetate (3.5 g, 42.82 mmol). The reaction mixture was continued to be stirred at 80 °C for 2 hours. At the end of the reaction, the mixture was cooled to 0 °C and stirred for 90 min to promote crystallization. The precipitate was collected by filtration and washed sequentially with a small amount of cold water and acetone to afford the target product 2-amino-4-hydroxypyrrolo[2,3-d]pyrimidine (11.9 g, quantitative yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 10.97 (s, 1H), 10.23 (s, 1H), 6.61-6.60 (m, 1H), 6.18-6.17 (m, 1H), 6.05 (s, 2H).

IC 50

DYRK1A

References

[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 21, p. 5596 - 5611
[2] European Journal of Organic Chemistry, 2010, # 34, p. 6517 - 6519
[3] Patent: CN103601779, 2016, B. Location in patent: Paragraph 0057; 0058; 0059
[4] Patent: CN104292117, 2016, B. Location in patent: Paragraph 0476; 0499-0501
[5] Patent: WO2014/11911, 2014, A2. Location in patent: Paragraph 00252; 00253; 00254