Triphenylphosphine → 5-methyl-3-{3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]benzyl}-3H-oxazolo[4,5-b]pyridin-2-one

HRID 1970884ノート

反応式

HRID 1970884 の反応式
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:20]=[N:21][C:22]([C:25]3[CH:26]=[C:27]([CH2:31]O)[CH:28]=[CH:29][CH:30]=3)=[N:23][CH:24]=2)[CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:31][C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([C:22]4[N:23]=[CH:24][C:19]([N:16]5[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]5)=[CH:20][N:21]=4)[CH:26]=3)[C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 100120755-Methyloxazolo[4,5-b]pyridin-2(3H)-oneHCID 59484860{3-[5-(4-Methylpiperazin-1-yl)pyrimidin-2-yl]phenyl}methanol

生成物 1

HCID 584861045-methyl-3-{3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]benzyl}-3H-oxazolo[4,5-b]pyridin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

67 mg (0.44 mmol) of 5-methyl-3H-oxazolo[4,5-b]pyridin-2-one and 125 mg (0.44 mmol) of {3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]phenyl}methanol are suspended in 5 ml of DMF with 222 mg (0.67 mmol) of polymer-bound triphenylphosphine (about 3 mmol of triphenylphosphine per g), and the mixture is shaken at room temperature for 30 min. 156 mg (0.67 mmol) of di-tert-butyl azodicarboxylate are added. The reaction mixture is shaken at room temperature for 15 h. The reaction mixture is filtered, the residue is evaporated, and the residue is purified by column chromatography on silica gel, giving 67 mg of “A125”; HPLC: Rt=2.20 min (method B); ESI: 418 (M+H);

後処理

  1. stirringThe reaction mixture is shaken at room temperature for 15 h
  2. filtrationThe reaction mixture is filtered
  3. customthe residue is evaporated
  4. customthe residue is purified by column chromatography on silica gel
  5. customgiving 67 mg of “A125”

出典と根拠

ORDレコード
ord-ac234d0ada944ff1a67316ad3eeb55a8
出典データセット
uspto-grants-2013_04
特許番号
US08431572B2

反応ノート

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