Sodium hydride → HCID 69750792, compound

HRID 586419Notes

Reaction equation

HRID 586419 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[N:24]=[C:23]([S:25][CH3:26])[N:22]=[C:21]([N:27]([CH3:29])[CH3:28])[CH:20]=1>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:12][C:19]2[CH:20]=[C:21]([N:27]([CH3:28])[CH3:29])[N:22]=[C:23]([S:25][CH3:26])[N:24]=2)[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 928923-BenzyloxyanilineHCID 4190857HCID 4190857, compound

Product 1

HCID 69750792HCID 69750792, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-(benzyloxy)aniline (5.13 g) and NaH (1.37 g) in tetrahydrofuran (15 mL) was refluxed for 30 minutes and then cooled to room temperature. A solution of N-[6-chloro-2-(methylsulfanyl)-4-pyrimidinyl]-N,N-dimethylamine (3.5 g) in tetrahydrofuran (35 mL) was added to this mixture and the resulting solution was stirred for 22.5 hours. The reaction mixture was quenched with saturated NH4Cl. Then the crude product was concentrated under reduced pressure and redissolved in EtOAc. The organic layer was separated and washed with aqueous citric acid (2×300 mL), water (2×300 mL) and brine (2×300 mL). The crude product was purified by column chromatography [eluent: EtOAc/hexane (1:4)], giving the desired product (5.9 g, 94%).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customThe reaction mixture was quenched with saturated NH4Cl
  3. concentrationThen the crude product was concentrated under reduced pressure
  4. dissolutionredissolved in EtOAc
  5. customThe organic layer was separated
  6. washwashed with aqueous citric acid (2×300 mL), water (2×300 mL) and brine (2×300 mL)
  7. customThe crude product was purified by column chromatography [eluent: EtOAc/hexane (1:4)]

Sources & evidence

ORD record
ord-809cc85687814eb48346f0730f525d85
Source dataset
uspto-grants-2005_08
Patent number
US06936607B2

Reaction notes

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