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Chemical Structure| 1016505-59-1 Chemical Structure| 1016505-59-1

Structure of 1016505-59-1

Chemical Structure| 1016505-59-1

7-Methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

CAS No.: 1016505-59-1

4.5 *For Research Use Only !

Cat. No.: A318899 Purity: 95%

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Product Details of [ 1016505-59-1 ]

CAS No. :1016505-59-1
Formula : C8H7N3O2
M.W : 177.16
SMILES Code : O=C(C1=C2N=CC=C(C)N2N=C1)O
MDL No. :MFCD09806068
InChI Key :ZDHMVXYJWKLOQS-UHFFFAOYSA-N
Pubchem ID :24688453

Safety of [ 1016505-59-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1016505-59-1 ]

* 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.

  • Downstream synthetic route of [ 1016505-59-1 ]

[ 1016505-59-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 5436-21-5 ]
  • [ 6994-25-8 ]
  • [ 1016505-59-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 60.0℃; for 0.25h; A mixture of ethyl 3-amino-4-pyrazolecarboxylate (250 mg), acetylacetaldehyde dimethyl acetale (200 μL) and concentrated hydrochloric acid (0.5 mL) was heated at 60 C. for 15 minutes. The resulting mixture was cooled and the solid which crashed out was collected by filtration, washed with ethyl acetate and dried in a vacuum oven to give 200 mg of 7-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid.
  • 2
  • ethyl 7-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]
  • [ 1016505-59-1 ]
YieldReaction ConditionsOperation in experiment
92% With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 25.0℃; for 2.0h; [0017] To a solution of ethyl 7-methylpyrazolo [1,5-a]pyrimidine-3-carboxylate (1.30 g, 6.33 mmol) in THF (8 mL), MeOH (6 mL), H2O (6 mL) was added LiOH.H2O (531 mg, 12.6 mmol) at 25 C. The mixture was stirred at 25 C for 2 hours. On completion, the mixture was concentrated in vacuo to remove THF. The aqueous phase was washed with EA (30 mL X 3) and acidified with 1 N HCl to pH=4. Then the aqueous phase was extracted with EA (80 mL x 5). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (1.04 g, 92% yield) as light yellow solid.1H NMR (400 MHz, DMSO-d6) δ 12.65 - 11.96 (m, 1H), 8.67 (d, J = 4.4 Hz, 1H), 8.58 (s, 1H), 7.20 (d, J = 4.4 Hz 1H) 2.76 (s 3H); LC-MS (ESI+) m/z 177.1 (M+H)+.
  • 3
  • [ 1016505-59-1 ]
  • 4-aminoadamantane-1-carbonitrile [ No CAS ]
  • N-(5-cyano-2-adamantyl)-7-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 4
  • trans-4-amino-1-hydroxyadamantane hydrochloride [ No CAS ]
  • [ 1016505-59-1 ]
  • N-(5-hydroxy-2-adamantyl)-7-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 5
  • [ 1016505-59-1 ]
  • 8-amino-2-(2-chloro-4-fluorophenyl)-2-azaspiro[4.5]decan-1-one [ No CAS ]
  • N-[(cis)-2-(2-chloro-4-fluorophenyl)-1-oxo-2-azaspiro[4.5]dec-8-yl]-7-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62 mg With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; To a solution of 8-amino-2-(2-chloro-4-fluorophenyl)-2-azaspiro[4.5]decan-1 -one (isomer 2) (75.0 mg, 253 pmol) in DMF (2.6 ml) was added PYBOP (145 mg, 278 pmol), N,Ndiisopropylethylamine (180 p1, 1.0 mmol) <strong>[1016505-59-1]7-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid</strong> (44.8 mg, 253 pmol) and the reaction was stirred for 16 hours at room temperature. For work-up sodium chloride solution (45 ml) was added and the resulting precipitate wasfiltrated. The residue was dissolved in DMSO and the crude product was purified by HP[C (Method 8) to give the title product (62 mg)[C-MS (Method 4): Rt = 1.09 mm; MS (ESIpos): m/z = 456 [M+H]1H-NMR (400 MHz, DMSO-d6) 6 (1.22), 1.573 (1.26), 1.580 (1.05),1.885 (0.98), 1.895 (1.20), 1.903 (1.98), 1.964 (1.16), 1.976 (1.05), 2.540 (1.21), 2.795 (15.89), 2.797[ppm]: 1.527 (1.10), 1.537 (1.18), 1.5481.788 (1.53), 1.798 (1.62), 1.809 (1.45),(1.74), 1.921 (2.07), 1.929 (2.86), 1.9442.066 (2.21), 2.074 (1.09), 2.083 (4.36),(16.00), 3.607 (2.79), 3.624 (5.14), 3.641(1.67), 1.5601.821 (1.22),(1.76), 1.9542.100 (2.27),(2.64), 4.054(0.80), 4.063 (0.84), 4.071 (0.80), 7.222 (2.73), 7.224 (2.60), 7.233 (2.63), 7.235 (2.80),7.285 (1.22), 7.292 (1.40), 7.306 (1.98), 7.314 (2.16), 7.327 (1.50), 7.334 (1.62), 7.474(2.73), 7.488 (2.87), 7.496 (2.40), 7.511 (2.22), 7.572 (2.58), 7.580 (2.73), 7.594 (2.65),7.601 (2.65), 8.144 (1.38), 8.164 (1.34), 8.196 (0.67), 8.589 (11.71), 8.690 (5.58), 8.701(5.32).
  • 6
  • [ 1016505-59-1 ]
  • 8-amino-2-(2-chlorophenyl)-2-azaspiro[4.5]decan-1-one [ No CAS ]
  • N-[(trans)-2-(2-chlorophenyl)-1-oxo-2-azaspiro[4.5]dec-8-yl]-7-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.3 mg With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃; for 24.0h; Benzotriazol- 1 -yl-oxytripyrrolidinophosphonium hexafluorophosphate (138 mg, 265 limol)and N,N-diisopropylethylamine (170 hI, 970 limol) were added to a mixture of 7-methylpyrazolo[1 ,5-a]pyrimidine-3-carboxylic acid (45.0 mg, 241 limol) and 8-amino-2-(2- chlorophenyl)-2-azaspiro[4.5]decan-1-one (isomer 1) (74.0 mg, 265 limol) in N,Ndimethylformamide (2.5 ml) and the mixture was stirred at room temperature for 24 h. For work-up, the reaction mixture was concentrated and the residue was purified by flashchromatography (25g lsolera-cartridge dichloromethane/methanol-gradient 0% -> 10% methanol) The crude product was recrystallized from diethyl ether to give the title compound (68.3 mg).LC-MS (Method 1): R = 1.07 mm; MS (ESIpos): m/z = 438.3 [M÷H] 1HNMR (400 MHz, DMSO-d6) 6 [ppm]: 1.463 (0.98), 1.487 (1.42), 1.504 (1.31), 1.535(0.64), 1.6741.732 (0.83),(2.81), 2.1693.000 (1.02),(0.69), 3.8317.233 (2.75),(2.02), 7.3867.414 (2.56),(1.57), 7.5768.724 (4.47).1.723 (1.65),(1.54), 2.1522.993 (0.58),(2.83), 3.8217.231 (2.70),(0.73), 7.3817.407 (8.06),(1.89), 7.5728.713 (4.88),(4.95),1.682(5.53),1.691(3.18),1.699(3.61),1.707 (3.12),1.740(0.77),1.962(1.75),1.971(1.82),1.993(1.70), 2.003(5.27),2.186(2.87),2.323(0.50),2.665(0.57),2.801 (16.00),3.009(1.00),3.016(0.57),3.625(3.00),3.642(5.24), 3.660(0.85),3.841(0.72),3.850(0.82),3.860(0.65),5.755 (0.85),7.242(2.63),7.244(2.74),7.358(0.66),7.369(1.32), 7.376(1.18),7.389(1.35),7.395(1.49),7.399(4.73),7.404 (7.35),7.417(3.00),7.421(1.17),7.554(1.91),7.558(3.11), 7.561(2.46),7.579(1.54),7.897(2.29),7.917(2.24),8.593 (9.94),
 

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