5H-Dibenzo[a,d]cyclohepten-5-one → 5-(2,4-bis(1,1-dimethylethoxy)pyrimidin-5-yl)-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 1531913

Reaction equation

Br[C:2]1[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:4][C:5]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[N:6][CH:7]=1.C([Li])CCC.[CH:23]1[C:33]2[CH:32]=[CH:31][C:30]3[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=3[C:28](=[O:38])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:10][C:9]([CH3:12])([O:8][C:5]1[N:4]=[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]([C:28]2([OH:38])[C:29]3[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=3[CH:31]=[CH:32][C:33]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]2=3)=[CH:7][N:6]=1)[CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the product of step (i) (50 g) in dry tetrahydrofuran (11) at −78° C. was added n-butyllithium (69 ml of a 2.5 M solution in hexanes) dropwise. After 0.5 hours a solution of 5H-dibenzo[a,d]cyclohepten-5-one (44 g) in tetrahydrofuran (100 ml) was added. The reaction mixture was stirred at −78° C. for three hours and then allowed to warm to room temperature overnight. Saturated aqueous ammonium chloride solution (400 ml) was added and the mixture extracted with ethyl acetate. The organic solution was dried (MgSO4) and evaporated under reduced pressure to give the crude 5-[2,4-bis[1,1-dimethylethoxy]pyrimidin-5-yl]-5H-dibenzo[a,d]cyclohepten-5-ol which was used directly.

Workup

temperatureto warm to room temperature overnight
extractionthe mixture extracted with ethyl acetate
dry with materialThe organic solution was dried (MgSO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-b67e701fdc6a4dd4ae5231942ef25189
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200981B1

Linked notes

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