[ CAS No. 58347-49-2 ]

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2D
Chemical Structure| 58347-49-2
Chemical Structure| 58347-49-2
Structure of 58347-49-2

Quality Control of [ 58347-49-2 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 58347-49-2 ]

SDS

Product Details of [ 58347-49-2 ]

CAS No. :58347-49-2MDL No. :MFCD04035684
Formula :C6H4ClN3Boiling Point :-
Linear Structure Formula :-InChI Key :-
M.W :153.57Pubchem ID :12281647
Synonyms :

Computed Properties of [ 58347-49-2 ]

TPSA : 30.2 H-Bond Acceptor Count : 2
XLogP3 : 1.3 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 58347-49-2 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58347-49-2 ]

  • Upstream synthesis route of [ 58347-49-2 ]

[ 58347-49-2 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
71% at 90℃; PREPARATION 32
7-Chloropyrazolo[1,5-a]pyrimidine
Pyrazolo[1,5-a]pyrimidin-7(4H)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88 mL, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 mL, 0.74 mmols) were mixed and stirred at 90ºC overnight.
It was poured onto water/ice, extracted with dichloromethane and washed with brine.
It was dried, filtered and concentrated in vacuo.
It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1) to afford the expected compound (83 mg, 71percent).
LRMS (m/z): 154 (M+1)+
1H NMR (400 MHz, DMSO-d6) d ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d, 1 H) 8.52 (d, 1 H)
71% at 90℃; Pyrazolo[1 ,5-a]pyrimidin-7(4/-/)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88 mL, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13 mL, 0.74 mmols) were mixed and stirred at 90°C overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1 ) to afford the expected compound (83 mg, 71 percent).LRMS (m/z): 154 (M+1 )+ 1H NMR (400 MHz, DMSO-d6) δ ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d, 1 H) 8.52 (d, 1 H)
71% at 90℃; PREPARATION 897-Chloropyrazolo[1 ,5-a]pyrimidinePyrazolo[1 ,5-a]pyrimidin-7(4H)-one (0.50g, 3.70 mmols), phosphorus oxychloride (0.88ml, 9.62 mmols) and diisopropylethylamine (DIEA, 0.13ml, 0.74 mmols) were mixed and stirred at 90°C overnight. It was poured onto water/ice, extracted with dichloromethane and washed with brine. It was dried, filtered and concentrated in vacuum. It was purified by chromatography (Silica gel, Hexane/Ethyl acetate 9:1 ) to afford the expected compound (83mg, 71 percent).LRMS (m/z): 154 (M+1 )+ 1 H N MR (400 MHz, DMSO-d6) d ppm 6.93 (d, 1 H) 7.43 (d, 1 H) 8.37 (d , 1 H) 8.52 (d, 1 H)
65% at 90℃; for 2.50 h; 7-Hydroxypyrazolo[1 ,5-a]pyrimidine (60 g, 444 mmol), phosphorus oxychloride (108 mL, 1.15 mol) and dimethylaniline (10.8 mL, 89 mmol) were added to a 250 mL round- bottomed flask and the contents heated to 90 0C. After 2.5 h, the reaction mixture was allowed to cool and was concentrated. The black residue was poured into a beaker containing crushed ice (600 mL) and the resulting solution kept cold using an ice bath. The aqueous solution was extracted with CH2CI2 (3 χ 150 mL) and the combined organic phase was washed with brine (100 mL). The organic phase was dried and concentrated to yield the desired crude product, 7-chloropyrazolo[1 ,5-a]pyrimidine, (44.2 g, 65percent) as a red solid. As the crude product was sufficiently pure to use in the subsequent step, a small sample was purified by column chromatography (33-66percent EtOAc/hexane) to yield an analytical sample as a white solid. HPLC 95percent; 1H NMR (250 MHz, CDCI3) δ 8.41 (d, J = 4.5 Hz, 1 H), 8.25 (d, J = 2.3 Hz, 1 H)1 6.99 (d, J ~ 4.5 Hz, 1 H), 6.84 (d, J = 2.3 Hz, 1 H); 13C NMR (62.9 MHz, CDCI3) δ 150.0, 148.2, 145.4, 139.0, 108.0, 98.7; MS (APCI) 154 [M+Hf.
47% for 72.00 h; The compound prepared in preparative example 1 (2.4 g, 17.4 mmol) was stirred in POCl3 (54 mL) and N,N-dimethylaniline (6.7 mL) 3 days. The reaction mixture was concentrated, dissolved in saturated NaHCO3 (2000 mL) and extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography using a 2.5percent MeOH in CH2Cl2 solution as eluent (1.3 g, 47percent yield): M+H=154.

Reference: [1] Patent: EP2518071, 2012, A1. Location in patent: Page/Page column 38
[2] Patent: WO2012/146667, 2012, A1. Location in patent: Page/Page column 90
[3] Patent: WO2012/146666, 2012, A1. Location in patent: Page/Page column 160
[4] Patent: WO2007/17678, 2007, A1. Location in patent: Page/Page column 44
[5] Journal of Medicinal Chemistry, 1981, vol. 24, # 5, p. 610 - 613
[6] Patent: US2007/82901, 2007, A1. Location in patent: Page/Page column 21
[7] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
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Reference: [1] Patent: US2012/122838, 2012, A1. Location in patent: Page/Page column 80
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Reference: [1] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
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  • [ 58347-49-2 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 11, p. 2516 - 2527
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