Diisopropylethylamine → 2-Methoxy-N-(6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-yl)acetamide

HRID 2069143노트

반응식

HRID 2069143 반응식
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[CH3:31][O:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[CH3:31][O:32][CH2:33][C:34]([NH:21][C:17]1[CH:16]=[C:15]([O:14][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:20]=[CH:19][N:18]=1)=[O:35]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 585325356-(4-Nitronaphthalen-1-yloxy)pyrimidin-4-amine

생성물 1

HCID 708814402-Methoxy-N-(6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-yl)acetamide수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-amine (350 mg, 1.24 mmol) in DCM (10.0 mL) and DIPEA (433 μL, 2.48 mmol) at 0° C. was added 2-methoxyacetyl chloride (170 μL, 1.860 mmol). The mixture was warmed to RT and after 3 hr the reaction was quenched by the addition of a solution of NH3 in MeOH (7M, 20 mL) and after a further 10 min was evaporated in vacuo. The residue was partitioned between DCM (30 mL) and saturated aq NaHCO3 solution (30 mL) and the organic layer was separated and washed with brine (30 mL) and then dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, MeOH in DCM, 0-100%, gradient elution) to furnish the title compound as a yellow solid (400 mg, 86%); Rt 4.60 min (Method 1 basic); m/z 355 (M+H)+ (ES+).

후처리

  1. customwas quenched by the addition of a solution of NH3 in MeOH (7M, 20 mL) and after a further 10 min
  2. customwas evaporated in vacuo
  3. customThe residue was partitioned between DCM (30 mL) and saturated aq NaHCO3 solution (30 mL)
  4. customthe organic layer was separated
  5. washwashed with brine (30 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (SiO2, 40 g, MeOH in DCM, 0-100%, gradient elution)

출처 및 근거

ORD 기록
ord-6befa2ee158b4bfa8f6891c9c2ae10dd
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299074B2

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