4,6-Dichloropyrimidine → HCID 11503607, compound

HRID 2264577Notes

Reaction equation

HRID 2264577 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:13]2=3)=[O:11])[CH:6]=[CH:7][CH:8]=1.[Cl:26][C:27]1[CH:32]=[C:31](Cl)[N:30]=[CH:29][N:28]=1>CC(C)=O.O.[OH-].[Na+].CCOC(C)=O>[F:25][C:2]([F:24])([F:1])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]3[CH:19]=[C:20]([O:23][C:31]4[CH:32]=[C:27]([Cl:26])[N:28]=[CH:29][N:30]=4)[CH:21]=[CH:22][C:13]2=3)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 2

HCID 709434,6-DichloropyrimidineHCID 86618286HCID 86618286, compound

Product 1

HCID 11503607HCID 11503607, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1.00 g (2.85 mMol) of 7-hydroxy-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide (Step 6.2) and 447 mg (3.0 mMol) 4,6-dichloro-pyrimidine in 8 ml acetone, 5 ml H2O and 3 ml NaOH 1 M is stirred at rt for 5 h. The reaction mixture is diluted with water and EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 19:1→7:3→1:4) gives the title compound: m.p.: 120° C.; MS: [M+1]+=463/465; Anal.: C,H,N,F,Cl.

Workup

  1. customthe aqueous phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9d68bf64dfb143dd99a1c5e93a179394
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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