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[ CAS No. 64951-07-1 ] {[proInfo.proName]}

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Chemical Structure| 64951-07-1
Chemical Structure| 64951-07-1
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Product Details of [ 64951-07-1 ]

CAS No. :64951-07-1 MDL No. :MFCD10698087
Formula : C9H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FGZMTIBNGQUEDE-UHFFFAOYSA-N
M.W : 191.19 Pubchem ID :326099
Synonyms :

Calculated chemistry of [ 64951-07-1 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.07
TPSA : 56.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 1.67
Log Po/w (WLOGP) : 0.91
Log Po/w (MLOGP) : 0.48
Log Po/w (SILICOS-IT) : 0.57
Consensus Log Po/w : 1.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.844 mg/ml ; 0.00441 mol/l
Class : Soluble
Log S (Ali) : -2.47
Solubility : 0.647 mg/ml ; 0.00338 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.2
Solubility : 1.21 mg/ml ; 0.00635 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.0

Safety of [ 64951-07-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 64951-07-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 64951-07-1 ]
  • Downstream synthetic route of [ 64951-07-1 ]

[ 64951-07-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 109-12-6 ]
  • [ 70-23-5 ]
  • [ 64951-07-1 ]
  • [ 64951-06-0 ]
YieldReaction ConditionsOperation in experiment
30% at 75℃; for 16 h; 2-Aminopyrimidine (5 g, 52.6 mmol) and bromoethyl pyruvate (90percent, 7.35 mL, 52.6 mmol) were dissolved in ethanol (80 mL) and the reaction was heated to 75 °C for 16 h. The reaction was concentrated under reduced pressure and diluted with CH2Cl2 and sat aq NaHCO3. The organic layer was washed with sat aq NaHCO3 (2x) and the aq layers were extracted with CH2Cl2 (3x). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting brown oil was suspended in cold CH2Cl2 and filtered. The filter cake was washed with cold CH2Cl2 to obtain ethyl imidazo[1,2-a]pyrimidine-2-carboxylate (3 g, 30percent) as a light yellow oil. The mother liquor contains a mixture of ethyl imidazo[1,2-a]pyrimidine-2- carboxylate and ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (6 g, 60percent) in the form of thick, black oil. This black oil was first purified by silica gel chromatography followed by recrystallization from EtOAc to obtain ethyl imidazo[1,2-a]pyrimidine-3- carboxylate (2 g, 20percent).[00236] For 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= 7.2 Hz, 3H). [00237] 13C NMR (500 MHz, CDCl3) δ 162.8, 152.2, 147.8, 137.7, 134.4, 115.3, 110.0, 61.2, 14.2.[00238] HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 0.99 min, 95percent homogeneity index. [00239] LCMS: Anal. Calcd. for C9H9N3O2 191.07 found: 192.13 (M+H)+.[00240] For 3-isomer: HPLC Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 1.39 min, 100percent homogeneity index. [00241] LCMS: Anal. Calcd. for C9H9N3O2 191.07 found: 192.19 (M+H)+.
Reference: [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
  • 2
  • [ 100422-78-4 ]
  • [ 64951-07-1 ]
Reference: [1] Tetrahedron, 1993, vol. 49, # 36, p. 8147 - 8158
[2] Australian Journal of Chemistry, 1994, vol. 47, # 7, p. 1249 - 1262
  • 3
  • [ 623-47-2 ]
  • [ 64951-07-1 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 22, p. 4837 - 4843
  • 4
  • [ 109-12-6 ]
  • [ 70-23-5 ]
  • [ 64951-07-1 ]
  • [ 64951-06-0 ]
YieldReaction ConditionsOperation in experiment
30% at 75℃; for 16 h; 2-Aminopyrimidine (5 g, 52.6 mmol) and bromoethyl pyruvate (90percent, 7.35 mL, 52.6 mmol) were dissolved in ethanol (80 mL) and the reaction was heated to 75 °C for 16 h. The reaction was concentrated under reduced pressure and diluted with CH2Cl2 and sat aq NaHCO3. The organic layer was washed with sat aq NaHCO3 (2x) and the aq layers were extracted with CH2Cl2 (3x). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting brown oil was suspended in cold CH2Cl2 and filtered. The filter cake was washed with cold CH2Cl2 to obtain ethyl imidazo[1,2-a]pyrimidine-2-carboxylate (3 g, 30percent) as a light yellow oil. The mother liquor contains a mixture of ethyl imidazo[1,2-a]pyrimidine-2- carboxylate and ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (6 g, 60percent) in the form of thick, black oil. This black oil was first purified by silica gel chromatography followed by recrystallization from EtOAc to obtain ethyl imidazo[1,2-a]pyrimidine-3- carboxylate (2 g, 20percent).[00236] For 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= 7.2 Hz, 3H). [00237] 13C NMR (500 MHz, CDCl3) δ 162.8, 152.2, 147.8, 137.7, 134.4, 115.3, 110.0, 61.2, 14.2.[00238] HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 0.99 min, 95percent homogeneity index. [00239] LCMS: Anal. Calcd. for C9H9N3O2 191.07 found: 192.13 (M+H)+.[00240] For 3-isomer: HPLC Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 1.39 min, 100percent homogeneity index. [00241] LCMS: Anal. Calcd. for C9H9N3O2 191.07 found: 192.19 (M+H)+.
Reference: [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
  • 5
  • [ 64951-07-1 ]
  • [ 149520-94-5 ]
YieldReaction ConditionsOperation in experiment
100% With hydrazine In ethanol at 75℃; for 16 h; To a stirred solution of ethyl imidazo[l ,2-α]pyrimidine-2-carboxylate or ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (1 g, 5.2 mmol) in ethanol (40 mL) was added hydrazine monohydrate (0.28 mL, 5.7 mmol). The reaction was heated to 75 °C for 16 h and was concentrated under reduced pressure. The resulting light yellow solid was suspended in diethyl ether and filtered to collect ethyl 2-amino-1H-imidazole-4- carboxylate (800 mg, 100percent) as a white solid. [00243] 1E NMR (400 MHz, CD3OD) 5 7.27 (s, 1H), 4.24 (q, J= 7.0 Hz, 2H), 1.31(t, J= 7.0 Hz, 3H).[00244] 13C NMR (500 MHz, CD3OD) δ 165.5, 156.1, 131.8, 125.7, 63.8, 17.3.[00245] HPLC Phenomenex LUNA C- 18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 0.46 min, 100percent homogeneity index.[00246] Anal. Calcd for C6H9N3O2: C, 46.44; H, 5.84; N5 27.08. Found: C, 46.17;H, 5.65; N, 27.28.[00247] HRMS: Anal. Calcd. for C6Hi0N3O2 156.0773 found: 156.0779 (M+H)+.
Reference: [1] Patent: WO2006/71752, 2006, A1, . Location in patent: Page/Page column 84
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