2-Amino-5-bromo-4-methylpyridine → 6-Amino-4-methylnicotinonitrile

HRID 644747

반응식

HRID 644747 반응식
Br[C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cu][C:11]#[N:12]>CN(C=O)C.CCOC(C)=O.O>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:11]#[N:12])=[C:3]([CH3:9])[CH:4]=1

참가 물질

6

반응물 2

HCID 8176952-Amino-5-bromo-4-methylpyridineHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 99641036-Amino-4-methylnicotinonitrile수율 32%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
200 °C

실험 절차

A mixture of 5-bromo-4-methyl-2-pyridinamine (0.50 g, 2.7 mmol) and copper (I) cyanide (0.263 g, 2.9 mmol) in DMF (12 mL) was heated at 200° C. for a total of 1.75 h in a microwave reactor. The reaction mixture was diluted with EtOAc and water. The resulting thick dark precipitate was filtered off. The filtrate was extracted with EtOAc (×3) and the combined extracts were dried and concentrated to give a dark yellow solid (0.115 g). The filter cake was and washed with 1:1 DCM/MeOH (1 L) which was concentrated to give a second batch of dark yellow solid (0.047 g). The filter cake was washed with 2M NH3 in MeOH (200 mL) which was concentrated to give a dark green solid (0.533 g). These 3 batches of solids were purified by column chromatography using 0-100% EtOAc/hexane as the eluent to give the title compound as a white solid (total yield: 0.213 g). δH (CDCl3, 400 MHz) 8.28 (1H, s), 6.36 (1H, s), 4.87 (2H, br.s), 2.40 (3H, s). MS (ES): MH+ 134.1.

후처리

  1. filtrationThe resulting thick dark precipitate was filtered off
  2. extractionThe filtrate was extracted with EtOAc (×3)
  3. customthe combined extracts were dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-547f55e5e8da4ca7a5b065a7887f6dde
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700599B2

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