1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-(4-Nitronaphthalen-1-yloxy)pyrimidin-4-amine

HRID 2069142노트

반응식

HRID 2069142 반응식
[NH2:1][C:2]1[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.C1CCN2C(=NCCC2)CC1.F[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([N+:31]([O-:33])=[O:32])=[CH:23][CH:22]=1>CS(C)=O.CO.C(O)(C(F)(F)F)=O>[N+:31]([C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([O:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[CH:3]=2)=[CH:22][CH:23]=1)([O-:33])=[O:32]

참가 물질

7

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2617641-Fluoro-4-nitronaphthaleneHCID 1354312726-Amino-1H-pyrimidin-4-one

생성물 1

HCID 585325356-(4-Nitronaphthalen-1-yloxy)pyrimidin-4-amine수율 16.8%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매2회HCID 887Methanol용매HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of 6-aminopyrimidin-4(3H)-one (866 mg, 7.79 mmol) in DMSO (10.0 mL) at RT was added DBU (1.29 mL, 8.57 mmol) and after 30 min a solution of 1-fluoro-4-nitronaphthalene (1.57 g, 8.18 mmol) in DMSO (3.0 mL) was added over 2 min. The resulting mixture was maintained at RT for 2 hr and was diluted with MeOH (20 mL) and TFA (2.0 mL) was added. The solution was subjected to SCX capture and release and the crude product so obtained was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 50-100%, gradient elution) to afford the title compound as a yellow solid (370 mg, 16.48%); Rt 3.82 min (Method 1 basic); m/z 283 (M+H)+ (ES+)

후처리

  1. additionwas added
  2. customthe crude product so obtained
  3. customwas purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 50-100%, gradient elution)

출처 및 근거

ORD 기록
ord-6bc6d103793d42b18b7c550772a9744a
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299074B2

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