(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine Chemical Properties

alpha 

-102 º (c=1%, EtOH)

Density 

1.028 g/mL at 20 °C (lit.)

Flash point:

85 °C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform and Ethanol

form 

Oil

pka

3.81±0.60(Predicted)

color 

Clear Colourless to Pale Yellow

optical activity

[α]20/D 102±5°, c = 1% in ethanol

BRN 

3542790

Boiling point:

100-102°C (20 hPa)

Stability:

Moisture Sensitive

InChI

InChI=1S/C9H16N2O2/c1-6(2)8-9(13-4)10-5-7(11-8)12-3/h6,8H,5H2,1-4H3/t8-/m1/s1

InChIKey

FCFWEOGTZZPCTO-MRVPVSSYSA-N

SMILES

[C@H]1(C(C)C)N=C(OC)CN=C1OC

CAS DataBase Reference

109838-85-9(CAS DataBase Reference)

Safety Information

Safety Statements 

23-24/25

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

F 

10

HS Code 

2933 99 80

MSDS

• Language:English Provider:SigmaAldrich

(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine Usage And Synthesis

Chemical Properties

Clear Colourless Liquid

Uses

(R)-3-Isopropyl-2,5-dimethoxy-3,6-dihydropyrazineChiral auxiliary for the synthesis of α-amino acids. It is an inhibitor with antitumor activity.

Synthesis

Step A: Preparation of (R)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine: To a 2L round bottom flask was added (R)-3-isopropylpiperazine-2,5-dione (20.7 g, 133 mmol), trimethine oxonium tetrafluoroborate (49.0 g, 331 mmol), and dichloromethane (500 mL). The reaction mixture was stirred vigorously at room temperature and protected by nitrogen.After 18 h, the reaction mixture changed to a clarified solution and formed a very viscous yellow oil at the bottom of the flask. Trimethyloxonium tetrafluoroborate (19.6 g, 133 mmol) was added additionally and stirring was continued at room temperature.After 23 h, the reaction mixture was cooled in an ice bath and 200 g of ice and 100 mL of concentrated ammonium hydroxide solution (28%) were added slowly. Stirring was continued in the ice bath for 1 hr. The organic and aqueous layers were separated and the aqueous layer was extracted with dichloromethane (2 x 50 mL). The organic layers were combined, washed sequentially with saturated sodium bicarbonate solution (2 x 100 mL) and brine (100 mL), dried with anhydrous potassium carbonate, filtered through a pad of diatomaceous earth, and concentrated under reduced pressure to give 25.9 g of light brown oil. The crude product was purified by column chromatography (eluent: ether/pentane=1:4) to afford 17.464 g of the target compound (R)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine as a colorless oil in 71.5% yield.1H NMR (400 MHz, CDCl3) δ 4.08-3.94 (m, 3H), 2.95 (s, 3H) , 2.87 (s, 3H), 2.30-2.18 (m, 1H), 1.04 (d, J=7.03Hz, 3H), 0.76 (d, J=6.64Hz, 3H).

References

[1] Organic Process Research and Development, 2005, vol. 9, # 2, p. 185 - 187
[2] Patent: US2006/264431, 2006, A1. Location in patent: Page/Page column 20-21
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 2, p. 157 - 166

(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine(109838-85-9)Related Product Information

• ISOPROPYL LAURATE
• Isopropyl alcohol
• Diphenyldimethoxysilane
• Phenazine methosulfate
• Glipizide
• 1,1-Dimethoxyethane
• Dimethyldimethoxysilane
• 3-Chloropropyltrimethoxysilane
• 3-Mercaptopropyltriethoxysilane
• Trimethoxypropylsilane
• (2S)-(+)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
• Dimethoxymethane
• Ammonium dihydrogen phosphate
• 2-ISOPROPYLPYRAZINE
• (R)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine
• (R)-(-)-2-Amino-3-methyl-1-butanol
• (2R,5SR)-(-)-2,5-Dihydro-3,6-dimethoxy-2-isopropyl-5-methylpyrazine
• (R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine