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

HRID 1162205노트

반응식

HRID 1162205 반응식
[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]

참가 물질

5

반응물 3

HCID 24758Sodium hydride2회HCID 87885Chloromethyl pivalate2회HCID 1355106695-Methoxyquinazolin-4-ol

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cf3484ae2a9d4238951886dda1a91d04
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820683B2

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