Potassium Carbonate → HCID 18753284, compound

HRID 1838141Notes

Reaction equation

HRID 1838141 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[C:18]([CH3:20])[NH:17][C:16](=[O:21])[C:15]=3[N+:22]([O-:24])=[O:23])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:25]([Si:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36]Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:25]([Si:29]([CH3:30])([CH3:31])[O:32][CH2:33][CH2:34][CH2:35][CH2:36][O:21][C:16]1[C:15]([N+:22]([O-:24])=[O:23])=[C:14]([N:11]2[CH2:10][CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:13][CH2:12]2)[N:19]=[C:18]([CH3:20])[N:17]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3382519tert-Butyl(4-chlorobutoxy)dimethylsilaneHCID 135617194HCID 135617194, compound

Product 1

HCID 18753284HCID 18753284, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 8, the 6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methyl-5-nitro-3H-pyrimidin-4-one (example 7) was treated with tert.-butyl-(4-chlorobutoxy)dimethylsilane and potassium carbonate in N,N-dimethyl-formamide at 80° C. to yield the 4-[4-(tert-butyl-dimethyl-silanyloxy)-butoxy]-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methyl-5-nitro-pyrimidine as a yellowish oil; MS: [M+H]+=519; and the 3-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methyl-5-nitro-3H-pyrimidin-4 one as a yellowish oil; MS: [M+H]+=519.

Sources & evidence

ORD record
ord-04358ac6cda6426e95721fdce6867153
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

Loading…