Ammonium Chloride → 1-(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanol
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]=[O:10])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[N:3]=1.[CH3:24][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:10])[CH3:24])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To the solution of 2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidine-5-carbaldehyde (797 mg, 2.14 mmol) in THF (10 mL) was added methyl magnesium bromide (3.0 M in diethyl ether, 6.4 mL, 19.3 mmol) at −78° C. under nitrogen atmosphere. The reaction mixture was warmed to room temperature gradually, and stirred overnight. The reaction mixture was poured into 20 mL of saturated aqueous NH4Cl at 0° C., and partitioned between EtOAc (30 mL×2) and brine (10 mL×2). The collected organic extracts were dried over Na2SO4, concentrated in vacuo, and purified by silica gel chromatography (EtOAc/Hexanes: 30/70) to afford 1-(2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanol. MS (ES+): 390.0 (MH+).
Workup
- custompartitioned between EtOAc (30 mL×2) and brine (10 mL×2)
- dry with materialThe collected organic extracts were dried over Na2SO4
- concentrationconcentrated in vacuo
- custompurified by silica gel chromatography (EtOAc/Hexanes: 30/70)
Sources & evidence
- ORD record
- ord-a1cb0454758e4b6cb157d1f3c774f881
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592432B2
Reaction notes
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