Sodium hydride → (5-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

HRID 1162205ノート

反応式

HRID 1162205 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7](=[O:15])[NH:8][CH:9]=[N:10]2.[C:16]([O:22][CH2:23]Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:16]([O:22][CH2:23][N:8]1[C:7](=[O:15])[C:6]2[C:11](=[CH:12][CH:13]=[CH:14][C:5]=2[O:4][CH3:3])[N:10]=[CH:9]1)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]

参加物

5

反応物 3

HCID 24758Sodium hydride2 回HCID 87885Chloromethyl pivalate2 回HCID 1355106695-Methoxyquinazolin-4-ol

生成物 1

HCID 68496089(5-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

Sodium hydride (1.24 g, 60% in oil, 31 mmol) was added portion-wise to a solution of 5-methoxyquinazolin-4(3H)-one (5 g, 28.4 mmol; obtained as described in WO-96/09294) in anhydrous DMF (50 ml) while maintaining the temperature at 25° C. The mixture was stirred at room temperature for 30 minutes. Chloromethyl pivalate (4.45 ml, 31 mmol) was added at room temperature for 3 hours. Additional sodium hydride (0.12 g, 3 mmol) and chloromethyl pivalate (0.67 ml, 4.5 mmol) were added and the mixture was stirred another hour. After evaporation of the solvents under high vacuum, the mixture was diluted with water and extracted with DCM. After drying with magnesium sulfate and evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: ethyl acetate-petroleum ether, 6:4 to 8:2) to give (5-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate as a white solid (7.4 g, 90%); HPLC tR: 2.69 min; Mass spectrum MH+ 291.

後処理

  1. customobtained
  2. stirringthe mixture was stirred another hour
  3. customAfter evaporation of the solvents under high vacuum
  4. additionthe mixture was diluted with water
  5. extractionextracted with DCM
  6. dry with materialAfter drying with magnesium sulfate and evaporation of the solvents
  7. customthe residue was purified by chromatography on silica gel (eluant: ethyl acetate-petroleum ether, 6:4 to 8:2)

出典と根拠

ORDレコード
ord-cf3484ae2a9d4238951886dda1a91d04
出典データセット
uspto-grants-2010_10
特許番号
US07820683B2

反応ノート

読み込み中…