HCID 117823999, compound → 2-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-(methoxymethyl)pyrimidin-4-yl)propan-2-ol

HRID 59156Notes

Reaction equation

HRID 59156 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([C:22](=[O:24])[CH3:23])[CH:19]=[C:18]([CH2:25][O:26][CH3:27])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[CH3:28][Mg]Br>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([C:22]([OH:24])([CH3:28])[CH3:23])[CH:19]=[C:18]([CH2:25][O:26][CH3:27])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 117823999HCID 117823999, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 863448012-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-(methoxymethyl)pyrimidin-4-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-(methoxymethyl)pyrimidin-4-yl)ethanone (160 mg, 0.44 mmol) in tetrahydrofuran (20 mL) was added dropwise to an ice-cold solution of methylmagnesium bromide (3.11 mL, 4.35 mmol) in tetrahydrofuran (10 mL). The mixture was stirred on ice-bath for 30 minutes and quenched with ammonium chloride (sat, aq). The mixture was extracted with dichloromethane, the organic phase was passed through a phase separator containing 1 cm layer of magnesium sulfate and the eluate was concentrated in vacuum. The residue was purified preparative HPLC to give the title compound as a solid, 124 mg (74%).

Workup

  1. customquenched with ammonium chloride (sat, aq)
  2. extractionThe mixture was extracted with dichloromethane
  3. additioncontaining 1 cm layer of magnesium sulfate
  4. concentrationthe eluate was concentrated in vacuum
  5. customThe residue was purified preparative HPLC

Sources & evidence

ORD record
ord-7f7734983286425eb1d031fb3e8dfba8
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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