Sodium Hydroxide → 3-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

HRID 333833Notes

Reaction equation

HRID 333833 reaction equation
CN1C(=O)CC(=O)N(C)C1=O.[Cl:12][C:13]1[CH:18]=[C:17]([N:19](CC=C)CC=C)[CH:16]=[CH:15][C:14]=1[CH:26]([CH3:40])[C:27]([C:33]1[CH:38]=[CH:37][N:36]=[C:35]([Cl:39])[CH:34]=1)([OH:32])[C:28]([F:31])([F:30])[F:29].[OH-].[Na+]>C(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:19][C:17]1[CH:16]=[CH:15][C:14]([CH:26]([CH3:40])[C:27]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([Cl:39])[CH:34]=2)([OH:32])[C:28]([F:29])([F:30])[F:31])=[C:13]([Cl:12])[CH:18]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 69860Dimethylbarbituric acidHCID 574212893-(2-Chloro-4-diallylamino-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 866291093-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-olYield 76.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1,3-dimethylbarbituric acid ([CAS Reg. No. 769-42-6], 828 mg), tetrakis(triphenylphosphine) palladium (0) (230 mg) and 3-(2-Chloro-4-diallylamino-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (590 mg) in DCM (120 ml) was heated under reflux for 3 h. NaOH (1N aq) was added and extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane 0:100-50:50) to give the title compound as a light yellow gum (370 mg). MS (m/e)=365.0 [M+H+].

Workup

  1. temperatureunder reflux for 3 h
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane 0:100-50:50)

Sources & evidence

ORD record
ord-d58ce1897b754bd99e6b451a7d5a2c50
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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