2,6-Diaminopyridine → HCID 11203277、化合物

HRID 1894932ノート

反応式

HRID 1894932 の反応式
Br[CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[C:7]([CH2:11]Br)[C:6]([CH2:13][CH3:14])=[C:5]([CH2:15]Br)[C:4]=1[CH2:17][CH3:18].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[NH2:26][C:22]1[N:21]=[C:20]([NH:19][CH2:2][C:3]2[C:8]([CH2:9][CH3:10])=[C:7]([CH2:11][NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=3)[C:6]([CH2:13][CH3:14])=[C:5]([CH2:15][NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=3)[C:4]=2[CH2:17][CH3:18])[CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 88612,6-DiaminopyridineHCID 11430Potassium CarbonateHCID 45893521,3,5-Tris(bromomethyl)-2,4,6-triethylbenzene

生成物 1

HCID 11203277HCID 11203277、化合物収率 40%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 1,3,5-tris(bromomethyl)-2,4,6-triethyl-benzene (0.79 g, 1.8 mmol), 2,6-diamino-pyridine (1.20 g, 11 mmol), and K2CO3 (0.79 g) in CH3CN (100 mL) was stirred at room temperature for 24 h and then heated under reflux for 2 h. After filtration of the reaction mixture and evaporation of CH3CN, the obtained powder was suspended in CHCl3. The suspension was filtrated, the chloroform solution was washed several times with water, dried, and the solvent was removed under reduced pressure. The crude product was crystallized from THF/hexane. Yield 40%. M.p. 164-165° C.; 1H NMR (500 MHz, CDCl3): δ=1.22 (t, 9H, J=7.5 Hz), 2.75 (q, 6H, J=7.5 Hz), 4.05 (t, 3H, J=4.2 Hz), 4.20 (s, 6H), 4.35 (d, 6H, J=4.2 Hz), 5.83-5.86 (m, 6H), 7.24 (m, 3H); 13C NMR (125 MHz, CDCl3): δ=16.9, 23.0, 40.6, 95.9, 96.9, 133.3, 139.4, 143.8, 157.8, 157.9; HR-MS calcd for C30H39N9: 525.3328; found: 525.3322. Rf=0.21 (CHCl3/CH3OH 7:1 v/v).

後処理

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. filtrationAfter filtration of the reaction mixture and evaporation of CH3CN
  4. filtrationThe suspension was filtrated
  5. washthe chloroform solution was washed several times with water
  6. customdried
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was crystallized from THF/hexane

出典と根拠

ORDレコード
ord-91ec6f38e2e84871b9a82295dd0e8199
出典データセット
uspto-grants-2013_08
特許番号
US08513420B2

反応ノート

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