Potassium Carbonate → HCID 87285339, compound

HRID 574266Notes

Reaction equation

HRID 574266 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C@H:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8]OS(C)(=O)=O)([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]1[CH:54]=[CH:53][CH:52]=[C:51]([C:55]([F:58])([F:57])[F:56])[C:24]=1[CH2:25][N:26]1[C:31]([CH3:32])=[C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH2:39][C:40]3[O:41][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:43][CH:44]=3)[CH2:35][CH2:34]2)[C:29](=[O:49])[NH:28][C:27]1=[O:50].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([Si:5]([CH3:20])([CH3:21])[O:6][C@H:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:8][N:28]1[C:29](=[O:49])[C:30]([N:33]2[CH2:34][CH2:35][N:36]([CH2:39][C:40]3[O:41][C:42]([C:45]([F:46])([F:47])[F:48])=[CH:43][CH:44]=3)[CH2:37][CH2:38]2)=[C:31]([CH3:32])[N:26]([CH2:25][C:24]2[C:51]([C:55]([F:57])([F:58])[F:56])=[CH:52][CH:53]=[CH:54][C:23]=2[F:22])[C:27]1=[O:50])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87285454HCID 87285454, compoundHCID 87285534HCID 87285534, compound

Product 1

HCID 87285339HCID 87285339, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethanol (85 mg, 0.337 mmol) in dichloromethane (2 mL) were added triethylamine (61 μl, 0.44 mmol) and methanesulfonyl chloride (27 μl, 0.35 mmol) in the order, followed by stirring at room temperature for 20 min. The solution was washed with an aqueous saturated sodium bicarbonate solution to separate an organic layer. The organic layer was dried over sodium sulfate and filtrated. The filtrate was concentrated and dried for 30 min in a vacuum to give methanesulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl ester. Methanesulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl ester, 1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-5-[4-(5-trifluoromethyl-furan-2-ylmethyl)-piperazin-1-yl]-1H-pyrimidine-2,4-dione (5-3) (60 mg, 0.112 mmol) and potassium carbonate (77 mg, 0.560 mmol) were dissolved at 70° C. for 12 hrs in DMF (1 ml) in a nitrogen atmosphere with stirring. The solution was cooled to room temperature, washed with an aqueous saturated sodium bicarbonate solution and concentrated. The residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate, 5/1) and dried in a vacuum to afford 83 mg of the compound as a white solid (yield 97%). 1H NMR (300 MHz, CDCl3) δ −0.23 (3H, s), −0.11 (3H, s), 0.80 (9H, s), 2.25 (2H, m), 2.33 (3H, s), 2.47 (2H, m), 2.80 (2H, m), 3.50-3.70 (2H, m), 3.62 (2H, s), 3.83 (1H, dd), 4.36 (1H, dd), 5.13 (1H, dd), 5.26-5.50 (2H, m), 6.30 (1H, d), 6.73 (1H, m), 7.16-7.43 (7H, m), 7.53 (1H, d)

Workup

  1. washwashed with an aqueous saturated sodium bicarbonate solution
  2. concentrationconcentrated
  3. customThe residue was purified
  4. customdried in a vacuum

Sources & evidence

ORD record
ord-c44117531ced4fc9ae1b7fec40045396
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

Loading…