2-Methoxyphenethyl bromide → HCID 44601136, compound

HRID 1520422Notes

Reaction equation

HRID 1520422 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:10]3[C:16](=[O:18])[CH:17]=2)=[N:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39]>O1CCCC1>[CH3:39][O:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][CH2:30][CH:15]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]2[C:16](=[O:18])[CH:17]=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][N:3]=3)[N:8]=[C:9]12

Participants

5

Reactant 3

HCID 5781992-Methoxyphenethyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 671776292-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-a]azepin-4-one

Product 1

HCID 44601136HCID 44601136, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.500 g (2.06 mmol) of 2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-α]azepin-4-one in dry tetrahydrofuran (20 mL) under argon at −30° C. was added 3.10 mL (3.10 mmol) of lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran). The solution was stirred at room temperature for 10 min and 1.31 mL of 1-(2-bromo-ethyl)-2-methoxy-benzene (8.25 mmol) was added. The reaction was stirred at 70° C. for 6 hours. The mixture was quenched with the addition of a saturated solution of ammonium chloride and extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (dichloromethane with 3% of methanol and 0.3% of ammonia) to afford 0.087 g of a solid (11%).

Workup

  1. stirringThe reaction was stirred at 70° C. for 6 hours
  2. customThe mixture was quenched with the addition of a saturated solution of ammonium chloride
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (dichloromethane with 3% of methanol and 0.3% of ammonia)

Sources & evidence

ORD record
ord-14a1572b418e428ba41773ef1a299024
Source dataset
uspto-grants-2015_07
Patent number
US09073914B2

Reaction notes

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