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[ CAS No. 31402-54-7 ]

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Chemical Structure| 31402-54-7
Chemical Structure| 31402-54-7
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CAS No. :31402-54-7 MDL No. :MFCD07368227
Formula : C5H6BrN3 Boiling Point : 283.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :188.03 g/mol Pubchem ID :13098184
Synonyms :

Safety of [ 31402-54-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 31402-54-7 ]

  • Upstream synthesis route of [ 31402-54-7 ]
  • Downstream synthetic route of [ 31402-54-7 ]

[ 31402-54-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 32779-36-5 ]
  • [ 74-89-5 ]
  • [ 31402-54-7 ]
YieldReaction ConditionsOperation in experiment
100% for 72 h; Reflux 40percent Aqueous methylamine solution (35 ml) and methanol (20 ml) were added to 5-bromo-2-chloropyrimidine (3 g, 15.5 mmol) and the resulting mixture was heated to reflux for 3 days. The mixture was cooled, then the solvent was evaporated under reduced pressure, the residue was partitioned with methylene chloride and 1 M sodium hydroxide, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (3.0 g, 100percent) as a white solid.1H-NMR (CDCl3) δ: 2.98 (3H, d, J=5.12 Hz), 5.16 (1H, brs), 8.29 (2H, s).
98% With potassium carbonate In tetrahydrofuran; water; <i>tert</i>-butyl alcohol at 150℃; for 0.25 h; microwave 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol), methylamine (41 percent in water, 2.00 mL, 23.78 mmol) and potassium carbonate (1.43 g, 10.34 mmol) in tert-butanol (4 mL)/THF (4 mL) are stirred for 15 min at 1500C in a microwave reactor. The crude mixture is diluted with DCM, the organic phase is washed with semi-saturated potassium carbonate solution and water, dried, filtered and evaporated down. Yield: 1.90 g (98 percent).
93%
Stage #1: at 115℃; for 48 h; Sealed vessel
Stage #2: With sodium hydroxide In dichloromethane; water
[0238] Methylamine (2.0 M in methanol, 4O mL, 80 mmol) was added to 5- bromo-2-chloropyrirnidine (5.6 g, 29.0 mmol) in a sealable reaction vessel. After allowing to vent for a few minutes, the vessel was sealed, placed behind a safety shield and heated in a 115 0C oil bath for 48 hours. Upon cooling the volatiles were removed in vacuo. The material was dissolved in CH2Cl2 (200 mL) and washed with IM NaOH (4O mL). The aqueous layer was extracted further with CH2Cb (2x50 mL). The combined organics were dried over MgSO4, filtered and concentrated yielding an off white solid (5.1 g, 93percent). LCMS (m/z): 188.0/190.0 (MH+).
93%
Stage #1: at 115℃; for 48 h; Sealed tube
Stage #2: With sodium hydroxide In dichloromethane; water
Synthesis -Aminomethyl-5-bromopyrimidine[0083] Methylamine (2.0 M in methanol, 40 mL, 80 mmol) was added to 5-bromo-2- chloropyrimidine (5.6 g, 29.0 mmol) in a sealable reaction vessel. After allowing to vent for a few minutes, the vessel was sealed, placed behind a safety shield and heated in a 115 °C oil bath for 48 hours. Upon cooling the volatiles were removed in vacuo. The material was dissolved in CH2C12 (200 mL) and washed with 1M NaOH (40 mL). The aqueous layer was extracted further with CH2C12 (2x50 mL). The combined organics were dried over MgSC>4, filtered and concentrated yielding an off white solid (5.1 g, 93percent). LCMS (m/z):188.0/190.0 (MH ).
90% at 60℃; for 6 h; To 5-bromo-2-chloropyrimidine (2g, 10.34mmol) was added 1 M methylamine solution in THF (20ml). The contents were stirred at 6O0C for 6h after which TLC confirmed the absence of the reactant. The contents were allowed to cool down. The volatiles were evaporated under reduced pressure and the residue was subjected to flash chromatography (hexane/ethyl acetate) to get (5-bromo-pyrimidin- 2-yl)-methyl-amine (1.75g, 90percent). This material was taken through Stage C (as described above) to get methyl-[5-(4,4,5,5,-tetramethyl-[1 ,3,2]dioxaborolan-2- yl]amine.

Reference: [1] Patent: US2010/130492, 2010, A1, . Location in patent: Page/Page column 93
[2] Patent: WO2010/12747, 2010, A1, . Location in patent: Page/Page column 16-17
[3] Patent: WO2007/84786, 2007, A1, . Location in patent: Page/Page column 90
[4] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 34 - 38
[5] Patent: WO2012/109423, 2012, A1, . Location in patent: Page/Page column 18
[6] Patent: WO2009/93981, 2009, A1, . Location in patent: Page/Page column 105
[7] Patent: WO2006/79791, 2006, A1, . Location in patent: Page/Page column 42
[8] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10033 - 10046
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  • [ 74-88-4 ]
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  • [ 38696-21-8 ]
YieldReaction ConditionsOperation in experiment
20%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 4.5 h;
Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N- dimethylpyrimidin-2-amine (compound 0601-117)A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0°C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0°C for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3 x 30 mL). The combined organic layers was washed with brine, dried over Na2S04, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]+; 1HNMR (400 MHz, DMSO-<3/4) δ 2.75 (d, J= 4.8 Hz, 3H), 7.35 (d, J= 4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49percent) as a yellow solid, LCMS: 202 [M+l]+; 1HNMR (400 MHz, DMSO-<3/4) δ 3.12 (s, 6H), 8.43 (s, 2H).
20%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 4.5 h;
Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N-dimethylpyrimidin-2-amine (compound 0601-117)[0353]A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0° C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0° C. for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3×30 mL). The combined organic layers was washed with brine, dried over Na2SO4, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]+; 1HNMR (400 MHz, DMSO-d6) δ 2.75 (d, J=4.8 Hz, 3H), 7.35 (d, J=4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49percent) as a yellow solid, LCMS: 202 [M+1]+; 1HNMR (400 MHz, DMSO-d6) δ 3.12 (s, 6H), 8.43 (s, 2H).
20%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 4.5 h;
5-bromo-pyrimidine-2-amine (3.48g, 20mmol) and a mixture of DMF (20mL) was cooled to 0 . NaH (60percent, 1.44g, 36mmol) to the mixture was added. After 15 minutes, then 0.5 hours with stirring at O ° C. was added iodoethane (5 mL, 80 mmol), the mixture was further warmed to room temperature for 4 hours. With the addition of water (30mL) and extracted with ethyl acetate (3x30mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated and purified by column chromatography (petroleum ether in ethyl acetate, 10percent v / v) on silica gel to give the two compounds: Compound 0601 the -116 as a white solid (0.76g, 20percent)
Reference: [1] Patent: WO2011/130628, 2011, A1, . Location in patent: Page/Page column 173
[2] Patent: US2013/102595, 2013, A1, . Location in patent: Paragraph 0352; 0353
[3] Patent: JP2015/187145, 2015, A, . Location in patent: Paragraph 0310
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Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069
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  • [ 593-51-1 ]
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Reference: [1] Patent: WO2006/44823, 2006, A2, . Location in patent: Page/Page column 197
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  • [ 31402-54-7 ]
  • [ 5388-21-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2692 - 2703
  • 6
  • [ 7752-82-1 ]
  • [ 74-88-4 ]
  • [ 31402-54-7 ]
  • [ 38696-21-8 ]
YieldReaction ConditionsOperation in experiment
20%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 4.5 h;
Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N- dimethylpyrimidin-2-amine (compound 0601-117)A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0°C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0°C for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3 x 30 mL). The combined organic layers was washed with brine, dried over Na2S04, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]+; 1HNMR (400 MHz, DMSO-<3/4) δ 2.75 (d, J= 4.8 Hz, 3H), 7.35 (d, J= 4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49percent) as a yellow solid, LCMS: 202 [M+l]+; 1HNMR (400 MHz, DMSO-<3/4) δ 3.12 (s, 6H), 8.43 (s, 2H).
20%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 4.5 h;
Step 39a: 5-Bromo-N-methylpyrimidin-2-amine (compound 0601-116) and 5-bromo-N,N-dimethylpyrimidin-2-amine (compound 0601-117)[0353]A mixture of 5-bromopyrimidin-2-amine (3.48 g, 20 mmol) and DMF (20 mL) was cooled to 0° C. To the mixture NaH (60percent, 1.44 g, 36 mmol) was added. After 15 minutes, iodomethane (5 mL, 80 mmol) was added and stirred at 0° C. for 0.5 h and the mixture was warmed to room temperature for additional 4 hours. Water (30 mL) was added and extracted with ethyl acetate (3×30 mL). The combined organic layers was washed with brine, dried over Na2SO4, concentrated and purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10percent v/v) to give two compounds: compound 0601-116 (0.76 g, 20percent) as a white solid, LCMS: 190 [M+2]+; 1HNMR (400 MHz, DMSO-d6) δ 2.75 (d, J=4.8 Hz, 3H), 7.35 (d, J=4.0 Hz, 1H), 8.34 (s, 2H); compound 0601-117 (1.96 g, 49percent) as a yellow solid, LCMS: 202 [M+1]+; 1HNMR (400 MHz, DMSO-d6) δ 3.12 (s, 6H), 8.43 (s, 2H).
20%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 4.5 h;
5-bromo-pyrimidine-2-amine (3.48g, 20mmol) and a mixture of DMF (20mL) was cooled to 0 . NaH (60percent, 1.44g, 36mmol) to the mixture was added. After 15 minutes, then 0.5 hours with stirring at O ° C. was added iodoethane (5 mL, 80 mmol), the mixture was further warmed to room temperature for 4 hours. With the addition of water (30mL) and extracted with ethyl acetate (3x30mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated and purified by column chromatography (petroleum ether in ethyl acetate, 10percent v / v) on silica gel to give the two compounds: Compound 0601 the -116 as a white solid (0.76g, 20percent)
Reference: [1] Patent: WO2011/130628, 2011, A1, . Location in patent: Page/Page column 173
[2] Patent: US2013/102595, 2013, A1, . Location in patent: Paragraph 0352; 0353
[3] Patent: JP2015/187145, 2015, A, . Location in patent: Paragraph 0310
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