Trifluoroacetic acid → 5-(5h-Dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

HRID 1871964

Reaction equation

HRID 1871964 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[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH:20]=[CH:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)=[CH:7][N:6]=1)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH:27]1[C:18]2[CH:19]=[CH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH:16]([C:8]3[C:9](=[O:11])[NH:10][C:5](=[O:4])[NH:6][CH:7]=3)[C:17]=2[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 212508825-(2,4-bis(1,1-dimethylethoxy)pyrimidin-5-yl)-5H-dibenzo[a,d]cyclohepten-5-ol

Product 1

HCID 110986755-(5h-Dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the 5-(2,4-bis(1,1-dimethylethoxy)pyrimidin-5-yl)-5H-dibenzo[a,d]cyclohepten-5-ol and triethylsilane (64 ml) in dry dichloromethane (400 ml) at 0° C. was added trifluoroacetic acid (150 ml) dropwise over ten minutes. The cooling bath was removed and the solution was stirred at room temperature overnight. Toluene (300 ml) was added and solution was evaporated under vacuum. The residue was azeotroped with toluene (3 times). The oil was treated with diethyl ether and the precipitated product collected as a white powder (44 g).

Workup

  1. customThe cooling bath was removed
  2. additionToluene (300 ml) was added
  3. customsolution was evaporated under vacuum
  4. customThe residue was azeotroped with toluene (3 times)
  5. additionThe oil was treated with diethyl ether
  6. customthe precipitated product collected as a white powder (44 g)

Sources & evidence

ORD record
ord-f3e86daa6b7640d6946c5abe9950cbe6
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Linked notes

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