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[ CAS No. 74290-69-0 ]

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2D
Chemical Structure| 74290-69-0
Chemical Structure| 74290-69-0
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Product Details of [ 74290-69-0 ]

CAS No. :74290-69-0MDL No. :MFCD08705763
Formula : C5H6BrN3 Boiling Point : 273.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :188.03Pubchem ID :21785149
Synonyms :

Computed Properties of [ 74290-69-0 ]

TPSA : 51.8 H-Bond Acceptor Count : 3
XLogP3 : 0.9 H-Bond Donor Count : 1
SP3 : 0.20 Rotatable Bond Count : 0

Safety of [ 74290-69-0 ]

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

Application In Synthesis of [ 74290-69-0 ]

  • Upstream synthesis route of [ 74290-69-0 ]
  • Downstream synthetic route of [ 74290-69-0 ]

[ 74290-69-0 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
36% With N-Bromosuccinimide In water; dimethyl sulfoxide at 20℃; for 5.25 h; Inert atmosphere; Cooling with ice Compound 10: 5-Bromo-6-methyl-pyrazin-2-ylamine. Under inert condition, to a solution 6-amino-2-methylpyrazine (100 mg, 1.0 equiv.) in a mixture of DMSO (4.6 mL) and water (0.2 mL) cooled by an ice bath, NBS (179 mg, 1.1 equiv.) was added in 3 portions. The light yellow mixture was stirred for 15 minutes, and then for 5 hrs at room temperature. The reaction mixture was hydrolysed with NaHCO3 saturated solution (25 mL) and extracted with EtOAc (30 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated. Purification by flash-chromatography afforded compound 10 as a light yellow solid in 36percent yield. 1H-NMR (400 MHz, DMSO): 2.34 (bs, 3H, C-CH3); 6.52 (bs, 2H, NH2); 7.49 (s, 1H, Ar). M/Z (M[79Br]+H)+ = 188.2.
36% With N-Bromosuccinimide In water; dimethyl sulfoxide at 20℃; for 5 h; Under inert condition, to a solution 6-amino-2-methylpyrazine (100 mg, 1.0 equiv.) in a mixture of DMSO (4.6 ml) and water (0.2 ml) cooled by an ice bath, NBS (179 mg, 1.1 equiv.) was added in 3 portions. The light yellow mixture was stirred for 15 minutes, and then for 5 hrs at room temperature. The reaction mixture was hydrolysed with NaHCO3 saturated solution (255 ml) and extracted with EtOAc (30 ml). The organic layer was washed with brine, dried over Na2SO4 and concentrated. Purification by flash-chromatography afforded compound 10 as alight yellow solid in 36percent yield. 1H-NMR (400 MHz, DMSO): 2.34 (bs, 3H, C-CH3); 6.52 (bs, 2H, NH2); 7.49 (s, 1H, Ar). M/Z(M[79Br]+H)+ = 188.2.
Reference: [1] Patent: EP2666775, 2013, A1, . Location in patent: Paragraph 02222
[2] Patent: WO2013/174822, 2013, A1, . Location in patent: Page/Page column 86
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Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147
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Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147
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  • [ 74290-69-0 ]
  • [ 74290-66-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147
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