Dimethyl Sulfoxide → N-methyl-4-(2-(4-((4-phenylphthalazin-1-yl)methyl)phenoxy)pyridin-3-yl)pyrimidin-2-amine

HRID 593964ノート

反応式

HRID 593964 の反応式
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH3:15])[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:16]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)=[N:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>CCOC(C)=O>[CH3:15][NH:14][C:10]1[N:9]=[C:8]([C:7]2[C:2]([O:39][C:36]3[CH:35]=[CH:34][C:33]([CH2:32][C:25]4[C:26]5[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:22]([C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=5)=[N:23][N:24]=4)=[CH:38][CH:37]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:12][N:11]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 161090044-(2-chloro-3-pyridinyl)-N-methyl-2-pyrimidinamineHCID 577562584-((4-Phenylphthalazin-1-yl)methyl)phenol

生成物 1

HCID 57756268N-methyl-4-(2-(4-((4-phenylphthalazin-1-yl)methyl)phenoxy)pyridin-3-yl)pyrimidin-2-amine

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

To a mixture of 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine (0.0500 g, 0.23 mmol), 4-((4-phenylphthalazin-1-yl)methyl)phenol (0.071 g, 0.23 mmol) and cesium carbonate (0.15 g, 0.45 mmol) was added DMSO (0.5 mL). The resulting mixture was heated to 130° C. in a sealed tube for 15 hours, then diluted with EtOAc and extracted with saturated sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude concentrate was purified by Gilson reverse-phase HPLC (0.1% TFA in ACN/water; 15-95% ACN; 40 mL/min). Diluted product with DCM and extracted with saturated sodium bicarbonate. Dried organics over sodium sulfate, filtered and concentrated. Lyophilized concentrate to obtained N-methyl-4-(2-(4-((4-phenylphthalazin-1-yl)methyl)phenoxy)pyridin-3-yl)pyrimidin-2-amine as a white solid. MS m/z=497 [M+H]+. Calc'd for C31H24N6O: 496.58.

後処理

  1. extractionextracted with saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationThe crude concentrate
  6. customwas purified by Gilson reverse-phase HPLC (0.1% TFA in ACN/water; 15-95% ACN; 40 mL/min)
  7. extractionDiluted product with DCM and extracted with saturated sodium bicarbonate
  8. filtrationDried organics over sodium sulfate, filtered
  9. concentrationconcentrated
  10. concentrationLyophilized concentrate

出典と根拠

ORDレコード
ord-f2b01a216d4041f2aaed71096852ddf0
出典データセット
uspto-grants-2016_01
特許番号
US09242961B2

反応ノート

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