1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Azidomethyl)-2-methylpyrimidine

HRID 657748

반응식

HRID 657748 반응식
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][N:3]=1.C1C=CC(OP(OC2C=CC=CC=2)([N:19]=[N+:20]=[N-:21])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(Cl)Cl.O>[N:19]([CH2:8][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=1)=[N+:20]=[N-:21]

참가 물질

7

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 14686706(2-Methylpyrimidin-5-yl)methanol

생성물 1

HCID 545950225-(Azidomethyl)-2-methylpyrimidine

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

A solution of (2-methylpyrimidin-5-yl)methanol (0.82 g, 6.6 mmol) in toluene (30 mL) and methylene chloride (40 mL) at 0° C. was treated with diphenylphosphonic azide (2.8 mL, 13 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (2.0 mL, 13 mmol) and stirred at 0° C. for 2 h. After being further stirred at rt for 16 h, the reaction mixture was diluted with water (50 mL) and methylene chloride (50 mL). The organic layer was separated and washed with brine, dried (Mg2SO4), filtered, and concentration. The residue was purified by silica gel column to yield a colorless oil.

후처리

  1. stirringAfter being further stirred at rt for 16 h
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Mg2SO4)
  5. filtrationfiltered
  6. concentrationconcentration
  7. customThe residue was purified by silica gel column
  8. customto yield a colorless oil

출처 및 근거

ORD 기록
ord-3d3d0b07d9b84da49fe303d46f429500
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076345B2

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