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Chemical Structure| 871335-85-2
Chemical Structure| 871335-85-2
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Product Details of [ 871335-85-2 ]

CAS No. :871335-85-2 MDL No. :MFCD16249846
Formula : C6H5ClN4 Boiling Point : -
Linear Structure Formula :- InChI Key :XFDFMJYQFBHDMF-UHFFFAOYSA-N
M.W :168.58 Pubchem ID :58931410
Synonyms :

Safety of [ 871335-85-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 871335-85-2 ]

* 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 [ 871335-85-2 ]
  • Downstream synthetic route of [ 871335-85-2 ]

[ 871335-85-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 60025-06-1 ]
  • [ 871335-85-2 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine; hydrazine In 1,4-dioxane at 0 - 20℃; for 18 h; A solution of 1-(4,6-dichloropyrimidin-5-yl)ethanone (3.81 g, 19.9 mmol) in 90 mL of dioxane at 0 0C was treated with triethylamine (2.78 mL, 19.9 mmol) and hydrazine hydrate (1.16 mL, 23.9 mmol). After addition, the reaction was stirred for 18 h at rt. The mixture was filtered and the precipitate washed with dioxane. The combined organics were evaporated and chromatographed on silica gel, eluting with 30-35percent ethyl acetate/ hexanes to afford 2.98 g, (89percent) of 4-chloro-3-methyl-1 H-pyrazolo[3,4-d]pyrimidine; 1H NMR (500 MHz, DMSO-cfe) δ 8.71 (1H), 2.60 (3H) ppm.
89% With triethylamine; hydrazine In 1,4-dioxane at 0 - 25℃; for 18 h; Step 1 : A solution of 1-(4,6-dichloropyrimidin-5-yl)ethanone (3.81 g, 19.9 mmol) (see Clark et al., J.C.S. Perkin 1 , 1976, 1004) in dioxane (90 mL) was cooled to O0C, and the chilled solution was treated with TEA (2.78 mL, 19.9 mmol) and hydrazine hydrate (1.16 mL, 23.9 mmol). The reaction mixture was then stirred for 18 hr. at 25SC. The mixture was filtered and the precipitate washed with dioxane. The combined filtrates were concentrated, and the resultant residue was chromatographed on silica gel, eluting with 30-35percent ethyl acetate/ hexanes to provide 4-chloro-3-methyl-1 H-pyrazolo[3,4-d]pyrimidine (C24). Yield: 2.98 g, 89percent. 1H NMR (500 MHz, DMSO-d6) δ: 8.71 (1 H), 2.60 (3H) ppm.
Reference: [1] Patent: WO2006/90261, 2006, A1, . Location in patent: Page/Page column 79
[2] Patent: WO2008/12635, 2008, A2, . Location in patent: Page/Page column 84
  • 2
  • [ 2942-47-4 ]
  • [ 871335-85-2 ]
YieldReaction ConditionsOperation in experiment
43%
Stage #1: With oxalyl dichloride In chloroform for 8 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In chloroform; water
To 4-hydroxy-3-methyl-lH-pyrazolo[3,4-d]pyrimidine (270 mg, 1.80 mmol, R. Badger, Aust. J. Chem. 1965, 18, 1267-1270) in chloroform (5 mL) was added oxalyl chloride (0.23 mL, 2.68 mmol) and DMF (0.05 mL), and the mixture was refluxed for 8 h. Over the first 4 h reaction time, more oxalyl chloride (1.7 mL) and DMF (1.0 mL) was added in portions. The mixture was added into saturated sodium bicarbonate (50 mL), and extracted with ethyl acetate (3 x 30 mL). The organic layer was washed with 5percent lithium chloride (20 mL), water (20 mL), and brine (20 mL), dried with sodium sulfate, and concentrated to afford 4-chloro-3-methyl-lH-pyrazolo[3,4-d]pyrimidine (130 mg, 43percent yield) as a brown solid. 1H NMR (400 MHz, d6-DMSO) 8 8.75 (s, 1H), 2.64 (s, 3H) ; MS (ESI) for C6H5ClN4: 169 (MH+).
Reference: [1] Patent: WO2005/117909, 2005, A2, . Location in patent: Page/Page column 57
  • 3
  • [ 60025-06-1 ]
  • [ 302-01-2 ]
  • [ 871335-85-2 ]
Reference: [1] Patent: US2009/5359, 2009, A1, . Location in patent: Page/Page column 19
  • 4
  • [ 2942-47-4 ]
  • [ 871335-85-2 ]
Reference: [1] Patent: US2009/48274, 2009, A1, . Location in patent: Page/Page column 7
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