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[ CAS No. 169749-99-9 ] {[proInfo.proName]}

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Chemical Structure| 169749-99-9
Chemical Structure| 169749-99-9
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Product Details of [ 169749-99-9 ]

CAS No. :169749-99-9 MDL No. :MFCD00191310
Formula : C12H18N2 Boiling Point : -
Linear Structure Formula :- InChI Key :UEAYAIWNQQWSBK-LBPRGKRZSA-N
M.W : 190.28 Pubchem ID :10397666
Synonyms :

Safety of [ 169749-99-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 169749-99-9 ]

* 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 [ 169749-99-9 ]
  • Downstream synthetic route of [ 169749-99-9 ]

[ 169749-99-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 131852-53-4 ]
  • [ 169749-99-9 ]
YieldReaction ConditionsOperation in experiment
0.89% With lithium aluminium tetrahydride In tetrahydrofuran for 4 h; Reflux 720 mg of tert-butyl (S)-(1-benzylpyrrolidine-3-yl)carbamate was added to a 100-mL round-bottomed flask. After 11.5 mL of tetrahydrofuran and 623 mg of lithium aluminum hydride (LiAlH4) were sequentially added thereto, the reaction mixture was refluxed for about 4 hours and then cooled at 0°C. 1.16 mL of deionized water was slowly added to the reaction mixture while cooling. After the reaction mixture was stirred for about 5 minutes, 1.16 mL of a 15percent sodium hydroxide (NaOH) aqueous solution was added thereto. The reaction mixture was further stirred for about 5 minutes, and then 3.80 mL of deionized water was added thereto to terminate the reaction. The reaction mixture was filtered through a Celite™ 545 filter agent. The resulting filtrate was distilled under reduced pressure, and then the resulting residue was purified by flash column chromatography (MeOH:CH2Cl2:NH4OH=5:90:5). As a result, 440 mg of (S)-1-benzyl-N-methylpyrrolidine-3-amine was obtained with a yield of about 89.9percent. (0218) 440 mg of (S)-1-benzyl-N-methylpyrrolidine-3-amine was added to a 25-mL round-bottomed flask, and then 9.00 mL of deionized water and 373 mg of 6-chloro-7-deazapurine were sequentially added thereto. After 639 mg of potassium carbonate (K2CO3) was added to the reaction mixture, the reaction mixture was refluxed for about 36 hours and then cooled at room temperature. The reaction mixture was extracted three times with 40.0 mL of dichloromethane (CH2Cl2) to collect an organic phase. The collected organic phase was concentrated under reduced pressure, and the resulting residue was purified by flash column chromatography (MeOH:CH2Cl2=2:98). As a result, 544 mg of (S)-N-(1-benzylpyrrolidine-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidine-4-amine was obtained with a yield of about 76.6percent. (0219) 534 mg of (S)-N-(1-benzylpyrrolidine-3-yl)-N-methyl-7H-pyrrolo[2,3-d]pyrimidine-4-amine was added to a 25-mL round-bottomed flask and then dissolved with 5.00 mL of methanol. After 534 mg of a 10w/wpercent palladium/ carbon (Pd/C) was added thereto, a hydrogen-containing balloon was installed on the reaction flask. The reaction mixture was vigorously stirred overnight and then filtered through a Celite™ 545 filter agent. The resulting filtrate was concentrated under reduced pressure, and then the resulting residue was purified by flash column chromatography (MeOH:CH2Cl2=2:98). The resulting fraction was concentrated under reduced pressure and then further under vacuum. As a result, 250 mg of (S)-N-methyl-N-(pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was obtained with a yield of about 66.1percent. (0220) 150 mg of (S)-N-methyl-N-(pyrrolidine-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine was added to a 5-mL round-bottomed flask and then dissolved with 2.25 mL of n-butanol. After 0.0730 mL of ethyl cyanoacetate was added thereinto, the reaction mixture was treated with 0.0520 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and then heated at about 80°C for about 24 hours. After termination of the reaction, the reaction solution was distilled under reduced pressure to remove the solvent. The resulting residue was purified by flash column chromatography (MeOH:CH2Cl2=2:98). The resulting fraction was concentrated under reduced pressure and then further under vacuum. As a result, 140 mg of (S)-3-(3-(methyl(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amino)pyrrolidine-1-yl)-3-oxopropanenitrile was obtained with a yield of about 71.4percent. (0221) 1H NMR (400 MHz, CDCl3) 510.39 (s, 1H), 8.33 (s, 1H), 7.12 (d, J = 2.6 Hz, 1H), 6.60 (s, 1H), 5.89-5.56 (m, 1H), 3.96-3.72 (m, 2H), 3.69-3.49 (m, 2H), 3.46 (t, J = 5.4 Hz, 2H), 3.35 (d, J = 14.9 Hz, 3H), 2.40-2.13 (m, 2H). (0222) LRMS (ESI) calcd for (C14H16N6O + H+) 285.2, found 285.1.
Reference: [1] Patent: EP3327021, 2018, A1, . Location in patent: Paragraph 0216-0222
  • 2
  • [ 101385-90-4 ]
  • [ 169749-99-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4205 - 4213
  • 3
  • [ 101385-90-4 ]
  • [ 169749-99-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4205 - 4213
  • 4
  • [ 116143-02-3 ]
  • [ 169749-99-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4205 - 4213
  • 5
  • [ 116183-79-0 ]
  • [ 169749-99-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4205 - 4213
  • 6
  • [ 116183-80-3 ]
  • [ 74-89-5 ]
  • [ 169749-99-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4205 - 4213
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