Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate Chemical Properties

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

2.70±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H9N3O2/c1-2-14-8(13)7-6-11-9-10-4-3-5-12(7)9/h3-6H,2H2,1H3

InChIKey

FGZMTIBNGQUEDE-UHFFFAOYSA-N

SMILES

C12=NC=C(C(OCC)=O)N1C=CC=N2

Safety Information

HS Code 

2933599590

Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate Usage And Synthesis

Synthesis

2-Aminopyrimidine (5 g, 52.6 mmol) and ethyl 3-bromopyruvate (90% purity, 7.35 mL, 52.6 mmol) were dissolved in ethanol (80 mL) and the reaction mixture was heated to 75°C for 16 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and diluted with an aqueous solution of dichloromethane (CH2Cl2) and saturated sodium bicarbonate (NaHCO3). The organic layer was washed twice with saturated aqueous NaHCO3 and the aqueous layer was extracted three times with CH2Cl2. The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The brown oil obtained was suspended in cold CH2Cl2, filtered, and the filter cake was washed with cold CH2Cl2 to give ethyl imidazo[1,2-a]pyrimidine-2-carboxylate (3 g, 30% yield) as a light yellow oil. The mother liquor contained a mixture of ethyl imidazo[1,2-a]pyrimidine-2-carboxylate and ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (6 g, 60% yield) as a viscous black oil. This black oil was first purified by silica gel column chromatography and then recrystallized from ethyl acetate (EtOAc) to give pure ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (2 g, 20% yield). For the 2-isomer: 1H NMR (500 MHz, CDCl3) δ 8.69 (dd, J = 2.2,6.6 Hz, 1H), 8.67 (dd, J = 2.2,4.4 Hz, 1H), 8.22 (s, 1H), 7.01 (dd, J = 3.9,6.6 Hz, 1H), 4.46 (q, J = 7.2 Hz, 2H). 1.43 (t, J = 7.2Hz, 3H).13C NMR (500MHz, CDCl3) δ162.8,152.2,147.8,137.7,134.4,115.3,110.0,61.2,14.2.HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100% B, 4 min, 1 min hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 0.99 min, 95% homogeneity index.LCMS: Analysis. Calculated.Measured result for C9H9N3O2 191.07 Measured value: 192.13 (M + H)+. For the 3-isomer: HPLC Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100% B, 4 min, 1 min retention time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 1.39 min, 100% homogeneity index. lcms: calc. 191.07 measured value for C9H9N3O2: 192.19 (M + H)+.

References

[1] Patent: WO2006/71752, 2006, A1. Location in patent: Page/Page column 83
[2] European Journal of Medicinal Chemistry, 1994, vol. 29, # 4, p. 279 - 286
[3] European Journal of Medicinal Chemistry, 1991, vol. 26, # 1, p. 13 - 18
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5620 - 5628
[5] Patent: WO2018/11628, 2018, A1. Location in patent: Paragraph 00266

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