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Chemical Structure| 1453176-67-4 Chemical Structure| 1453176-67-4

Structure of 1453176-67-4

Chemical Structure| 1453176-67-4

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Product Details of [ 1453176-67-4 ]

CAS No. :1453176-67-4
Formula : C8H7N3O2
M.W : 177.16
SMILES Code : O=C(C1=NC2=CC=NN2C=C1)OC
MDL No. :MFCD29905277
InChI Key :FCZKDRQJWFMUNZ-UHFFFAOYSA-N
Pubchem ID :89784976

Safety of [ 1453176-67-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 1453176-67-4 ]

* 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.

  • Downstream synthetic route of [ 1453176-67-4 ]

[ 1453176-67-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 29274-24-6 ]
  • [ 1453176-67-4 ]
YieldReaction ConditionsOperation in experiment
52% With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 100.0℃; under 7600.51 Torr; A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% With triethylamine; at 100.0℃; under 7600.51 Torr;Sealed tube; A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 100.0℃; under 7600.51 Torr;Sealed tube; A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1 .00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(U) dichloride (1 g, 1.42 mmol, 0.1 1 equiv) was stirred in a 100-mL pressure reactor overnight at 100 "C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1 .2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1 .09 min, m/z 178.0 [M+H]
52% With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 100.0℃; under 7600.51 Torr; [0211] Step 3. Pyrazolo[1,5-alpyrimidine-5-carboxylic acid methyl ester. A mixture of 5- chloro-pyrazolo[1,5-a]pyrimidine (2 g, 13.02 mmol, 1.00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.11 equiv) was stirred in a 100-mL pressure reactor overnight at 100 C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum.The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:5) to yield 1.2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.09 mi m/z = 178.0 [M+Hf?.
52% With bis-triphenylphosphine-palladium(II) chloride; triethylamine; at 100.0℃; under 7600.51 Torr; [0219] Step 3. PyrazolorL5-alpyrimidine-5-carboxylic acid methyl ester. A mixture of 5- chloro-pyrazolo[l,5-a]pyrimidine (2 g, 13.02 mmol, 1.00 equiv), triethylamine (4 mL), methanol (80 mL), and bis(triphenylphosphine)palladium(II) dichloride (1 g, 1.42 mmol, 0.11 equiv) was stirred in a 100-mL pressure reactor overnight at 100 C under 10 atmospheres of carbon monoxide. The reaction mixture was cooled to rt then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 :5) to yield 1.2 g (52%) of the title compound as a light yellow solid. LC/MS (Method I, ESI): RT= 1.09 min, m/z = 178.0 [M+H]+.

  • 3
  • [ 1453176-67-4 ]
  • [ 1086375-50-9 ]
YieldReaction ConditionsOperation in experiment
87% With hydrogenchloride; acetic acid; In water; at 120.0℃; for 3.0h; Step 4 To a solution of methyl <strong>[1453176-67-4]pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester</strong> ( 1 00 mg, 0.56 mmol, 1 .00 equiv) in acetic acid (5 mL) was added concentrated HCl (37%, 5 mL). The resulting solution was stirred for 3 h at 120 C, then concentrated under vacuum. The residue was dissolved in 3 mL of water and then adjusted to pH 5 with saturated aqueous sodium carbonate solution. The precipitated product was collected by filtration then air-dried to give 0.08 g (87%) of pyrazolo[1,5-a]pyrimidine-5-carboxylic acid as a light yellow solid. LC/MS (Method I, ESI): RT= 0.95 min, m/z = 164.0 [M+H]+
87% With hydrogenchloride; water; acetic acid; at 120.0℃; for 3.0h; Step 4 To a solution of methyl <strong>[1453176-67-4]pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester</strong> ( 1 00 mg, 0.56 mmol, 1 .00 equiv) in acetic acid (5 mL) was added concentrated HC1 (37%, 5 mL). The resulting solution was stirred for 3 h at 120 C, then concentrated under vacuum. The residue was dissolved in 3 mL of water and then adjusted to pH 5 with saturated aqueous sodium carbonate solution. The precipitated product was collected by filtration then air-dried to give 0.08 g (87%) of pyrazolo[1,5-a]pyrimidine-5-carboxylic acid as a light yellow solid. LC/MS (Method I, ESI): RT= 0.95 min, m/z = 164.0 [M+H]+
87% With hydrogenchloride; acetic acid; In water; at 120.0℃; for 3.0h; Step 4 To a solution of methyl <strong>[1453176-67-4]pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester</strong> ( 1 00 mg, 0.56 mmol, 1 .00 equiv) in acetic acid (5 mL) was added concentrated HCl (37%, 5 mL). The resulting solution was stirred for 3 h at 120 C, then concentrated under vacuum. The residue was dissolved in 3 mL of water and then adjusted to pH 5 with saturated aqueous sodium carbonate solution. The precipitated product was collected by filtration then air-dried to give 0.08 g (87%) of pyrazolo[1,5-a]pyrimidine-5-carboxylic acid as a light yellow solid. LC/MS (Method I, ESI): RT= 0.95 min, m/z = 164.0 [M+H]+
87% With hydrogenchloride; acetic acid; In water; at 120.0℃; for 3.0h; Intermediate 11: Pyrazolo [1,5-al pyrimidine-5-carboxylic acid [0212] Step 4. To a solution of methyl <strong>[1453176-67-4]pyrazolo[1,5-a]pyrimidine-5-carboxylic acid methyl ester</strong> (100 mg, 0.56 mmol, 1.00 equiv) in acetic acid (5 mL) was added concentrated HC1 (37%, 5 mL). The resulting solution was stirred for 3 h at 120 C, then concentrated under vacuum. The residue was dissolved in 3 mL of water and then adjusted to pH 5 with saturated aqueous sodium carbonate solution. The precipitated product was collected by filtration then air-dried to give 0.08 g (87%) of pyrazolo[1,5-a]pyrimidine-5-carboxylic acid as a light yellow solid. LC/MS (Method I, ESI): RT= 0.95 mi m/z = 164.0 [M+H].
87% With hydrogenchloride; acetic acid; In water; at 120.0℃; for 3.0h; [0220] Step 4. To a solution of methyl pyrazolo[l,5-a]pyrimidine-5-carboxylic acid methyl ester (100 mg, 0.56 mmol, 1.00 equiv) in acetic acid (5 mL) was added concentrated HC1 (37%, 5 mL). The resulting solution was stirred for 3 h at 120 C, then concentrated under vacuum. The residue was dissolved in 3 mL of water and then adjusted to pH 5 with saturated aqueous sodium carbonate solution. The precipitated product was collected by filtration then air-dried to give 0.08 g (87%) of pyrazolo[l,5-a]pyrimidine-5-carboxylic acid as a light yellow solid. LC/MS (Method I, ESI): RT= 0.95 min, m/z = 164.0 [M+H]+.

  • 4
  • [ 1453176-67-4 ]
  • [ 1454284-63-9 ]
 

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