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

HRID 2069142ノート

反応式

HRID 2069142 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 887Methanol溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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+)

後処理

  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)

出典と根拠

ORDレコード
ord-6bc6d103793d42b18b7c550772a9744a
出典データセット
uspto-grants-2012_10
特許番号
US08299074B2

反応ノート

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