2,6-Diaminopyridine → HCID 11203277, 화합물

HRID 1894932노트

반응식

HRID 1894932 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 11203277HCID 11203277, 화합물수율 40%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-91ec6f38e2e84871b9a82295dd0e8199
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513420B2

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