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

Reaction equation

HRID 324415 reaction equation
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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-81e57e3676454468b17fdd38b48e4ab2
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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