Ammonium Chloride → (2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanol

HRID 2046985Notes

Reaction equation

HRID 2046985 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.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[OH: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

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 582908822,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidine-5-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 58290857(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidine-5-carbaldehyde (112.3 mg, 0.3 mmol) in THF (1.0 mL) was added phenylmagnesiumbromide (3.0 M in diethyl ether, 1.0 mL, 3.0 mmol) at 0° C. under argon atmosphere. After addition, the reaction mixture was slowly warmed to room temperature and further stirred overnight. To the reaction mixture was then added 2.0 mL of saturated aqueous NH4Cl at 0° C., dissolved in EtOAc (50 mL) and washed with H2O (10 mL) and brine (10 mL). The organic phase was dried over Na2SO4, concentrated in vacuo, and purified by silica gel chromatography (eluent: EtOAc in Hexanes: 0 to 33%) to afford (2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanol as a colorless oil. MS (ES+): 452.0 (MH+).

Workup

  1. additionAfter addition
  2. washwashed with H2O (10 mL) and brine (10 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography (eluent: EtOAc in Hexanes: 0 to 33%)

Sources & evidence

ORD record
ord-94c1c0ad82ca4b2f9fdbb39c9d22647d
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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