Boron trifluoride etherate → (+/-)-5-(7-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedione

HRID 324415

반응식

HRID 324415 반응식
CC(C)([O:4][C:5]1[N:10]=[C:9]([O:11]C(C)(C)C)[C:8]([C:16]2(O)[C:22]3[N:23]=[C:24]([CH3:26])[O:25][C:21]=3[CH2:20][CH2:19][C:18]3[CH:27]=[C:28]([CH2:31][CH3:32])[CH:29]=[CH:30][C:17]2=3)=[CH:7][N:6]=1)C.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:31]([C:28]1[CH:29]=[CH:30][C:17]2[CH:16]([C:8]3[C:9](=[O:11])[NH:10][C:5](=[O:4])[NH:6][CH:7]=3)[C:22]3[N:23]=[C:24]([CH3:26])[O:25][C:21]=3[CH2:20][CH2:19][C:18]=2[CH:27]=1)[CH3:32]

참가 물질

6

반응물 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 70113732(+/-)-4-(2,4-Bis(1,1-dimethylethoxy)pyrimidin-5-yl)-7-ethyl-2-methyl-9,10-dihydro-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-ol

생성물 1

HCID 70114236(+/-)-5-(7-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A stirred solution of the product from step (i) (0.60 g) in dichloromethane (15 ml) was treated with triethylsilane (0.225 ml) and cooled to 0° C. Boron trifluoride etherate (0.65 ml) was added in four equal portions at 5 minute intervals and the reaction stirred at room temperature for 16 hours. The reaction was poured into saturated sodium bicarbonate solution (200 ml) and extracted with ethyl acetate. The extracts were dried (MgSO4) and evaporated to give a yellow solid which was purified by reverse phase chromatography eluting with 50% to 80% methanol in 0.1% aqueous ammonium acetate.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow solid which
  5. customwas purified by reverse phase chromatography
  6. washeluting with 50% to 80% methanol in 0.1% aqueous ammonium acetate

출처 및 근거

ORD 기록
ord-81e57e3676454468b17fdd38b48e4ab2
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218376B1

연결된 노트

불러오는 중…