Triphenylphosphine → 5-methyl-3-[3-(5-methylpyrimidin-2-yl)benzyl]-3H-benzoxazol-2-one

HRID 655324

反応式

HRID 655324 の反応式
[CH3:1][C:2]1N=[C:6]2[NH:8][C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:20]=[C:21]([CH2:25]O)[CH:22]=[CH:23][CH:24]=2)=[N:17][CH:18]=1.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[N:8]([CH2:25][C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([C:16]4[N:15]=[CH:14][C:13]([CH3:12])=[CH:18][N:17]=4)[CH:20]=3)[C:6]=2[CH:27]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 100120755-Methyloxazolo[4,5-b]pyridin-2(3H)-oneHCID 59484945[3-(5-Methylpyrimidin-2-yl)phenyl]methanol

生成物 1

HCID 251250955-methyl-3-[3-(5-methylpyrimidin-2-yl)benzyl]-3H-benzoxazol-2-one

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

112 mg (0.75 mmol) of 5-methyl-3H-oxazolo[4,5-b]pyridin-2-one, 180 mg (0.90 mmol) of [3-(5-methylpyrimidin-2-yl)phenyl]methanol and 238 mg (0.90 mmol) of triphenylphosphine are suspended in 5 ml of THF, and the mixture is stirred for 30 min. The mixture is subsequently cooled to 0° C., and 186 μl (0.90 mmol) of diisopropyl azodicarboxylate are added. The reaction mixture is stirred at room temperature for 2 h. The reaction mixture is diluted with 20 ml of dichloromethane, washed with 2×20 ml of water, dried over sodium sulfate and evaporated. The residue is purified by column chromatography on silica gel; yield: 101 mg of “A45”; ESI: 332 (M+H); Rt=4.91 min (method C);

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 2 h
  2. washwashed with 2×20 ml of water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-4e4fbdd9c9a34a518667459884621da4
出典データセット
uspto-grants-2011_12
特許番号
US08071593B2

関連ノート

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