ChemicalBook > CAS DataBase List > Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate

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

Product Name: Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate
CAS No.: 64951-07-1
Chemical Name: Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate
Synonyms: Nsc296230;ETHYL IMIDAZO[1,2-A]PYRIMIDINE-3-CARBOXYLATE;ethyl imidazo[1,2-a]pyrimidine-7-carboxylate;ETHYL IMIDAZO[1,2-A]PYRIMIDINE-3-CARBOXYLATE ISO 9001：2015 REACH
CBNumber: CB72460700
Molecular Formula: C9H9N3O2
Formula Weight: 191.19
MOL File: 64951-07-1.mol

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

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

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Safety

HS Code: 2933599590

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

TRC

Product number: E919213
Product name: Ethylimidazo[1,2-a]pyrimidine-3-carboxylate
Packaging: 100mg
Price: $65
Updated: 2021/12/16

AK Scientific

Product number: 7404AE
Product name: Ethylimidazo[1,2-a]pyrimidine-3-carboxylate
Packaging: 250mg
Price: $165
Updated: 2021/12/16

Matrix Scientific

Product number: 083655
Product name: Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate
Purity: 95%
Packaging: 1g
Price: $524
Updated: 2021/12/16

SynQuest Laboratories

Product number: 4H23-1-5S
Product name: Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate
Packaging: 1g
Price: $332
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0151907
Product name: ETHYL IMIDAZO(1,2-A)PYRIMIDINE-3-CARBOXYLATE
Purity: 95.00%
Packaging: 5MG
Price: $503.6
Updated: 2021/12/16

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

Synthesis

109-12-6

70-23-5

64951-07-1

64951-06-0

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

Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate Preparation Products And Raw materials

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View Lastest Price from Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: ETHYL IMIDAZO[1,2-A]PYRIMIDINE-3-CARBOXYLATE 64951-07-1
Price: US $1.10/g
Min. Order: 1g
Purity: 99.0% min
Supply Ability: 100 tons min
Release date: 2021-05-12

64951-07-1, Ethyl imidazo[1,2-a]pyrimidine-3-carboxylateRelated Search:

IMIDAZO[1,2-A]PYRIMIDINE-3-CARBALDEHYDE IMIDAZO[1,2-A]PYRIDIN-2-YLMETHANOL Imidazo[1,2-a]pyridine Methyl imidazo[1,2-a]pyridine-7-carboxylate Imidazo[1,2-b]pyridazine-6-carboxylic acid (9CI) IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID ETHYL ESTER Imidazo[1,2-a]pyridine-6-carbaldehyde IMIDAZO[1,2-A]PYRIDINE-3-CARBONITRILE Imidazo[1,5-a]pyridine-1-carboxaldehyde (9CI) C-IMIDAZO[1,5-A]PYRIDIN-1-YL-METHYLAMINE Imidazo[1,2-a]pyridine-2-acetic acid ethyl ester IMIDAZO[1,2-A]PYRIDINE-3-BORONIC ACID PINACOL ESTER IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID Imidazo[1,2-b]pyridazin-3-ylamine Imidazo[2,1-b]thiazol-5-ylmethanamine Imidazo[1,2-a]pyridine, HCl IMidazo[1,2-a]pyriMidine hydrochloride 5,6,7,8-Tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid ethyl ester

Nsc296230

ethyl imidazo[1,2-a]pyrimidine-7-carboxylate

ETHYL IMIDAZO[1,2-A]PYRIMIDINE-3-CARBOXYLATE

ETHYL IMIDAZO[1,2-A]PYRIMIDINE-3-CARBOXYLATE ISO 9001：2015 REACH

64951-07-1