1-(Bromomethyl)-2-(trifluoromethyl)benzene → HCID 66780526, compound

HRID 1958008Notes

Reaction equation

HRID 1958008 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[N:11]1([C:17]2[S:18][C:19]3[C:24](=[O:25])[N:23]=[CH:22][NH:21][C:20]=3[N:26]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.Br[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]([F:38])([F:37])[F:36]>O1CCCC1>[N:11]1([C:17]2[S:18][C:19]3[C:24](=[O:25])[N:23]=[CH:22][N:21]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]([F:36])([F:37])[F:38])[C:20]=3[N:26]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 2733832Lithium HexamethyldisilazideHCID 178518229HCID 178518229, compound

Product 1

HCID 66780526HCID 66780526, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (0.755 mL, 0.755 mmol) was added to a suspension of 2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (90 mg, 0.378 mmol) in tetrahydrofuran (THF) (3 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 30 min before the addition of 1-(bromomethyl)-2-(trifluoromethyl)benzene (0.069 mL, 0.453 mmol). The mixture was warmed up to RT and stirred overnight. The solvent was removed and the residue was partitioned between DCM and brine. The organic layer was concentrated and the residue was purified on a biotage column (5% MeOH/DCM) to give 80 mg (55%) of the product (the undesired regioisomer (24 mg, 17%) was less polar on silica gel). LCMS (ES) m/z=397.0 (M+H)+, 1H NMR (400 MHz, CDCl3-d1) δppm 8.05 (s, 1H), 7.76 (d, J=7.6 Hz, 1H), 7.45˜7.55 (m, 2H), 7.05 (d, J=7.6 Hz, 1H), 5.54 (s, 2H), 3.80 (m, 4H), 3.58 (m, 4H).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between DCM and brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified on a biotage column (5% MeOH/DCM)

Sources & evidence

ORD record
ord-a9067674d1f745429b663bf8168b9fea
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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