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[ CAS No. 74290-68-9 ]

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2D
Chemical Structure| 74290-68-9
Chemical Structure| 74290-68-9
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Product Details of [ 74290-68-9 ]

CAS No. :74290-68-9MDL No. :MFCD17011819
Formula : C5H6BrN3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :188.03Pubchem ID :21785148
Synonyms :

Computed Properties of [ 74290-68-9 ]

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 [ 74290-68-9 ]

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

Application In Synthesis of [ 74290-68-9 ]

  • Upstream synthesis route of [ 74290-68-9 ]
  • Downstream synthetic route of [ 74290-68-9 ]

[ 74290-68-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5521-58-4 ]
  • [ 74290-65-6 ]
  • [ 74290-68-9 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With hydrogen bromide; acetic acid In chloroform at 50℃; for 0.50 h; Darkness
Stage #2: With bromine In chloroform at 55℃; for 21.00 h;
Stage #3: With sodium carbonate In chloroform; water
A solution of HBr/CH3CO2H (360 g (260 mL), 1.50 mol, 33percent HBr in CH3CO2H) in anhydrous CHCl3 (300 mL) was added over 15 min to a solution of 5-methylpyrazin-2-amine 15 (42 g, 0.38 mmol) in CHCl3 (1 L). The reaction flask was wrapped in aluminum foil and heated to 50 °C for 30 min in the dark whereupon a solution of Br2 (68 g, 0.42 mmol) in CHCl3 (500 mL) was added dropwise over 3 h during which time the internal temperature of the reaction never exceeded 55 °C. After 18 h at 55 °C the solvent was evaporated under reduced pressure. The crude mixture was diluted with water (200 mL) and the pH was adjusted to pH=9 by the addition of solid Na2CO3. The suspension was filtered under vacuum and the filtrate was extracted with EtOAc (1 L.x.5). The combined organic extracts were concentrated under reduced pressure and purified by flash silica gel chromatography eluting with petroleum ether/EtOAc (5:1-->1:1) to give compound 6-bromo-5-methylpyrazin-2-amine 17a (36 g, 50percent) as a light orange solid; mp 154-157 °C; IR (KBr): 3315, 3188, 1744, 1638, 1575, 1482, 1375, 1308, 1051 cm-1; 1H NMR (400 MHz, CDCl3): δ=7.84 (s, 1H), 4.55 (br s, 2H), 2.52 (s, 3H); 13C NMR (100 MHz, CDCl3): δ=152.2, 141.8, 138.4, 129.2, 22.2; HRMS-ESI: calcd for C5H7BrN3 (M+H)+: 187.9823 and 189.9803; found: 187.9816 and 189.9796. An analytical sample of 3-bromo-5-methylpyrazin-2-amine (17b) was also isolated for spectroscopic analysis; mp 56-57 °C. 1H NMR (400 MHz, CDCl3): δ=7.80 (s, 1H), 4.95 (br s, 2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3): δ=150.6, 142.8, 139.9, 125.2, 19.7; HRMS-ESI: calcd for C5H7BrN3 (M+H)+: 187.9823 and 189.9803; found: 187.9817 and 189.9796.
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147
[2] Tetrahedron, 2011, vol. 67, # 47, p. 9063 - 9066
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